[ CAS No. 88196-70-7 ] {[proInfo.proName]}

Name: 88196-70-7|(R)-1-(3-Methoxyphenyl)ethanamine|98%
Brand: Ambeed
SKU: A534226
Price: 16.0 USD
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Limited Quantity	USD 15-60
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Inaccessible (Haz class 6.1), International	USD 150+
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Quality Control of [ 88196-70-7 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 88196-70-7 ]

Product Details of [ 88196-70-7 ]

CAS No. :	88196-70-7	MDL No. :	MFCD00671655
Formula :	C₉H₁₃NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CJWGCBRQAHCVHW-SSDOTTSWSA-N
M.W :	151.21	Pubchem ID :	7020759
Synonyms :

Calculated chemistry of [ 88196-70-7 ]

Physicochemical Properties

Num. heavy atoms :	11
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.33
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	45.41
TPSA :	35.25 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.12 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.04
Log Po/w (XLOGP3) :	1.55
Log Po/w (WLOGP) :	1.39
Log Po/w (MLOGP) :	1.53
Log Po/w (SILICOS-IT) :	1.6
Consensus Log Po/w :	1.62

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-2.03
Solubility :	1.43 mg/ml ; 0.00943 mol/l
Class :	Soluble
Log S (Ali) :	-1.9
Solubility :	1.9 mg/ml ; 0.0126 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.58
Solubility :	0.394 mg/ml ; 0.00261 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.53

Safety of [ 88196-70-7 ]

Signal Word:	Danger	Class:	8,6.1
Precautionary Statements:	P261-P273-P280-P305+P351+P338-P310	UN#:	2922
Hazard Statements:	H314-H331-H412	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 88196-70-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 88196-70-7 ]

[ 88196-70-7 ] Synthesis Path-Downstream 1~88

1
[ 586-37-8 ]
[ 88196-70-7 ]

Reference： [1]Journal of the American Chemical Society,2018,vol. 140,p. 2024 - 2027
[2]Bulletin of the Chemical Society of Japan,1993,vol. 66,p. 3414 - 3418
[3]Chemical Communications,2010,vol. 46,p. 5500 - 5502
[4]Tetrahedron Asymmetry,2012,vol. 23,p. 716 - 721
[5]Journal of Organic Chemistry,2013,vol. 78,p. 5314 - 5327
[6]Organic Letters,2016,vol. 18,p. 3258 - 3261
[7]European Journal of Organic Chemistry,2017,vol. 2017,p. 39 - 44
[8]Angewandte Chemie - International Edition,2019,vol. 58,p. 7329 - 7334
Angew. Chem.,2019,vol. 131,p. 7407 - 7412,6

2
[ 50919-07-8 ]
[ 88196-70-7 ]

Reference： [1]Tetrahedron Asymmetry,1996,vol. 7,p. 1539 - 1542
[2]Chemical Communications,1996,p. 2415 - 2416

3
N-[1-(3-Methoxy-phenyl)-ethyl]-oxalamic acid [ No CAS ]
[ 50919-07-8 ]
[ 88196-70-7 ]

Reference： [1]Chemical Communications,1996,p. 2415 - 2416

4
[ 185526-98-1 ]
[ 50919-07-8 ]
[ 88196-70-7 ]

Reference： [1]Chemical Communications,1996,p. 2415 - 2416

5
[ 7315-17-5 ]
[ 88196-70-7 ]
[3-(2-Chloro-phenyl)-prop-(E)-ylidene]-[(R)-1-(3-methoxy-phenyl)-ethyl]-amine [ No CAS ]

Reference： [1]Tetrahedron Letters,1998,vol. 39,p. 3451 - 3454

6
[ 21598-06-1 ]
[ 88196-70-7 ]
5-hydroxy-1H-indole-2-carboxylic acid [1-(3-methoxy-phenyl)-ethyl]-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 483 - 486

7
[ 586-37-8 ]
[ 50919-07-8 ]
[ 88196-70-7 ]

Reference： [1]Journal of the Chemical Society. Perkin Transactions 2 (2001),2000,p. 1339 - 1347
[2]Chemical Communications,2010,vol. 46,p. 5500 - 5502
[3]Chemical Communications,2010,vol. 46,p. 5500 - 5502
[4]Tetrahedron Asymmetry,2012,vol. 23,p. 716 - 721
[5]Green Chemistry,2017,vol. 19,p. 474 - 480
[6]Green Chemistry,2017,vol. 19,p. 474 - 480

8
[ 1643-28-3 ]
[ 88196-70-7 ]
[ 177172-48-4 ]

Yield	Reaction Conditions	Operation in experiment
93.8%	In toluene;	C. N-((R)-alpha-Methyl-3-methoxybenzyl)-3-(2-chlorobenzene) propanamide To a solution of toluene (6000 mL) under argon atmosphere was added beta2-chlorophenylpropionic acid (2930.7 g, 15.87 mol) and (R)-3-methoxy-alpha-methylbenzylamine (2045.4 g, 13.53 mol). The reaction was heated at reflux for 55 hours with azeotropic removal of water using a Dean-Stark trap. The reaction was allowed to cool and was then diluted with ethyl acetate (21.3 kg, 23.6 L). The organic solution was extracted with 10% hydrochloric acid (313.5 kg), 4% sodium hydroxide (313.5 kg) and brine (3*14 L). The organic phase was dried (Na2 SO4, 5 kg) and concentrated in vacuo. The resulting solid was dried under vacuum at 35+-2 C. for 22 hours to give N-((R)-alpha-methyl-3-methoxybenzyl)-3-(2-chlorobenzene)propanamide (4023.3, 93.8%) as a solid.

Reference： [1]Organic Letters,2016,vol. 18,p. 3258 - 3261
[2]Tetrahedron Letters,2001,vol. 42,p. 5029 - 5032
[3]Journal of Organic Chemistry,2004,vol. 69,p. 5595 - 5607
[4]Patent: US5504253,1996,A
[5]Tetrahedron Letters,2010,vol. 51,p. 3536 - 3537
[6]Applied Organometallic Chemistry,2011,vol. 25,p. 105 - 109
[7]ChemSusChem,2020,vol. 13,p. 1800 - 1807

9
[ 368447-74-9 ]
[ 88196-70-7 ]

Reference： [1]Tetrahedron Letters,2001,vol. 42,p. 5029 - 5032

10
[ 6575-13-9 ]
[ 88196-70-7 ]
[ 590-86-3 ]
[ 531512-50-2 ]
2-[2-(3,4-Dihydro-1H-isoquinolin-2-yl)-2-(4-methoxy-phenyl)-acetyl]-[(R)-1-(3-methoxy-phenyl)-ethyl]-amino}-4-methyl-pentanoic acid (2,6-dimethyl-phenyl)-amide [ No CAS ]

Reference： [1]Tetrahedron Letters,2003,vol. 44,p. 603 - 605

11
[ 24424-99-5 ]
[ 88196-70-7 ]
[ 871728-33-5 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

12
[ 50919-07-8 ]
[ 50919-07-8 ]
[ 88196-70-7 ]

Reference： [1]Tetrahedron Asymmetry,2005,vol. 16,p. 3807 - 3813
[2]Tetrahedron Asymmetry,2006,vol. 17,p. 259 - 267

13
[ 368447-74-9 ]
[ 25779-13-9 ]
[ 88196-70-7 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5595 - 5607

14
[ 81097-48-5 ]
[ 88196-70-7 ]
N-{2-[1-(3-methoxy-phenyl)-ethylamino]-cyclopentyl}-4-methyl-benzenesulfonamide [ No CAS ]

Reference： [1]Tetrahedron Letters,2005,vol. 46,p. 7935 - 7939

15
[ 624-31-7 ]
[ 88196-70-7 ]
[ 407-25-0 ]
(R)-(2-(4-methylphenyl))-α-methyl-5-methoxybenzyltrifluoroacetamide [ No CAS ]

Reference： [1]Organic Letters,2006,vol. 8,p. 5211 - 5213

16
[ 88196-70-7 ]
[ 4578-80-7 ]
[2-(4-Chloro-phenyl)-2-phenyl-ethyl]-[(R)-1-(3-methoxy-phenyl)-ethyl]-amine [ No CAS ]

Reference： [1]Australian Journal of Chemistry,2006,vol. 59,p. 445 - 456

17
C₂₈H₂₇NO₄ [ No CAS ]
[ 120-57-0 ]
[ 88196-70-7 ]
C₃₀H₃₄N₂O₄ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2005,vol. 13,p. 1829 - 1836

18
[ 88196-70-7 ]
tecalcet [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5595 - 5607
[2]Tetrahedron Letters,2001,vol. 42,p. 5029 - 5032
[3]Tetrahedron Letters,1998,vol. 39,p. 3451 - 3454
[4]Organic Letters,2016,vol. 18,p. 3258 - 3261

19
[ 368447-68-1 ]
[ 88196-70-7 ]

Reference： [1]Journal of Organic Chemistry,2004,vol. 69,p. 5595 - 5607
[2]Tetrahedron Letters,2001,vol. 42,p. 5029 - 5032

20
[ 88196-70-7 ]
[ 518060-42-9 ]

Yield	Reaction Conditions	Operation in experiment
		To the solution of (f?)-1-(3-Methoxy-phenyl)-ethylamine (0.5 g, 3.31 mmol) in DCM (25 mL) at -78 0C was added 1.0M BBr3 solution in DCM (6.6 mL, 6.62 mmol) dropwise. The solution was warmed to room temperature and the reaction mixture was quenched with methanol (100 mL) and then concentrated in vacuo. This process was repeated until no white fumes were observed upon addition of methanol to afford 3-((F?)-1-Amino-ethyl)- phenol as a pale yellow oil (0.51 g) which was used in the next step without further purification

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896
[2]Patent: WO2010/136755,2010,A1 .Location in patent: Page/Page column 67; 68

21
[ 88196-70-7 ]
[ 266369-69-1 ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

22
[ 88196-70-7 ]
(R)-[1-(3-morpholin-4-yl-phenyl)ethyl]-carbamic acid tert-butyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

23
[ 88196-70-7 ]
(R)-trifluoromethanesulfonic acid 3-(1-tert-butoxycarbonylamino-ethyl)-phenyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

24
[ 88196-70-7 ]
(E)-N-[(R)-1-(3-Morpholin-4-yl-phenyl)-ethyl]-3-phenyl-acrylamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

25
[ 88196-70-7 ]
(R)-1-(3-morpholin-4-yl-phenyl)ethylamine dihydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2004,vol. 47,p. 2887 - 2896

26
[ 88196-70-7 ]
5-hydroxy-1H-indole-2-carboxylic acid [1-(3-hydroxy-phenyl)-ethyl]-amide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 483 - 486

27
[ 4774-14-5 ]
[ 88196-70-7 ]
6-chloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]pyrazin-2-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
67%		In a procedure analogous to Example 1, reaction of [R-?-METHYLBENZYLAMINE] (1. Og, 6. [6MMOL)] and 2,6-dichloropyrazine (0. 440g. 2. 95mmol) furnished the product (517mg, [67%).] [1H-N.M.R.(CDCL3) No. ] 1. 59 (d, J=6.9Hz, 3H, C, 3. 81 [(S,] 3H, OCH3), 4.87 (m, [SH,] CH), 5.47 [(BR] [S,] 1H, NH), 6. 79-7.30 (m, 4H, Ar-H), 7.66 (s, 1H, pyraz-H), 7. 79 (s, 1H, pyraz-H).

Reference： [1]Patent: WO2003/99796,2003,A1 .Location in patent: Page 24

28
4-methoxy-3-(1,4-benzodioxan-5-yl)benzenecarboxaldehyde [ No CAS ]
[ 88196-70-7 ]
(R)-N-(1-(3-methoxyphenyl)ethyl)-N-(4-methoxy-3-(1, 4-benzodioxan-5-yl) lmethyl) amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from [4-METHOXY-3- (1,] 4-benzodioxan-5- yl) benzenecarboxaldehyde and [(R)-3-METHOXY-OC-METHYLBENZYLAMINE] according to general procedure C. [C25H27NO4] Mass (calculated): [405]; (found): [M+H+] = 406,255 NMR (400 MHz, CDC13) : 1.3 (3H, d, [J =] 6 Hz, NCHCH3) ; 3.55 and 3.65 (2H, dd, [J =] 12 Hz, CH2N) ; 3.75 (3H, s, CH30); 3.77 (3H, s, CH30) ; 3.75 [(1H,] m; [NCHME)] ; 4.2 (4H, s, [OCH2CH2O)] ; 6.7 [(1H,] dd, J = 1 and 8 Hz, aryl-H); 6. [8-6.] 9 (4H, m, aryl-H); 7.0 [(1H,] dd, dd, [J=] 1 and 8 Hz, aryl-H); 7.1 [(1H,] d, J = 1 Hz, aryl-H); 7.25-7. 3 (3H, m, aryl-H).

Reference： [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 54

29
[ 628710-94-1 ]
[ 88196-70-7 ]
(R)-N-(1-(3-methoxyphenyl)ethyl)-N-(4-methoxy-3-(2-methylbenzoxazol-5-yl)methyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from [4-METHOXY-3- (2-METHYLBENZOXAZOL-5-] yl) benzenecarboxyaldehyde and [(R)-3-METHOXY-?-METHYLBENZYLAMINE ] according to general procedure C. [C2SH26N203] Mass (calculated): [[402]] ; (found): [[M+H+]] = 403. NMR (400 MHz, [CDC13)] : 1.3 (3H, bd, J = 6 Hz, NCHCH3); 2.6 (3H, s, CH3) ; 3.55 and 3.6 (2H, dd, [J =] 12 Hz, CH2N) ; 3.7 (3H, s, [CH30)] ; 3.72 (3H, s, CH30); 3.75 [(1H,] q, [J=] 6 Hz; [NCHME)] ; 6.75 [(1H,] dd, [J= 1] and 8 Hz, aryl-H); 6.8-6. 9 (3H, m, aryl-H); 7.2-7. 3 (3H, m, aryl-H); 7.4 [(1H,] dd, J = 1 and 8 Hz, aryl-H); 7.45 [(1H,] d, J = 8 Hz, aryl-H); 7.7 [(1H,] d, J = 1 Hz, aryl-H).

Reference： [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 58

30
[ 628710-98-5 ]
[ 88196-70-7 ]
(R)-N-1-(1-(3-methoxyphenyl)ethyl)-N-(4-methoxy-3-(benzoxazo1-5-yl)methyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from [4-METHOXY-3- (BENZOXAZOL-5-YL)] benzene- carboxyaldehyde and [(R)-3-METHOXY-O-METHYLBENZYLAMINE] according to general procedure C. C24H24N203 Mass (calculated): [[388]] ; (found): [[M+H+]] = 389,891. NMR (400 MHz, CDC13) : 1.3 (3H, d, J = 6 Hz, NCHCH3) ; 2.6 (3H, s, CH3) ; 3.5 and 3.55 (2H, dd, J = 12 Hz, [CH2N)] ; 3.7-3. [8] (4H, m, CH30 and [NCHME)] ; 6.7 [(1H,] dd, J = 2 and 8 Hz, aryl-H) ; 6.8-6. 9 (3H, m, aryl-H); 7.15-7. 25 (3H, m, aryl- H); 7.45 [(1H,] dd, [J] = 1 and 8 Hz, aryl-H); 7.5 [(1H,] d, J = [8] Hz, aryl-H); 7.85 (1H, d, [J=] 1 Hz, aryl-H); 8 [(1H,] s, aryl-H).

Reference： [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 61

31
[ 628711-03-5 ]
[ 88196-70-7 ]
(R)-N-(1-(3-methoxyphenyl)ethyl)-N-(4-chloro-3-(4'-methoxyphenyl)-phenylmethyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from 4-chloro-3- (4-methoxyphenyl) benzene- carboxaldehyde and [(R)-3-METHOXY-A-METHYLBENZYLAMINE] according to general procedure C. [C23H23C1N02] Mass (calculated): [381]; (found): [[M+H+]] = 382,384 [(CL).] NMR (400 MHz, CDCl3) : 1.3 (3H, d, J = 6 Hz, NCHCH3) ; 3.55 and 3.6 (2H, dd, [J=12] Hz, [CH2N)] ; 3.7-3. 75 (4H, m, [NCHME] and [MEO)] ; 3.8 (3H, s, MeO) ; 6.75 [(1H, DD, J = 2] and [8] Hz, aryl-H) ; 7. 85 [(1H,] d, J = 1 Hz, aryl-H); 7.9 (2H, d, J = 8 Hz, aryl-H); 7.15 [(1H,] dd, [J= 1] and 8 Hz, aryl-H); 7.15-7. 25 (2H, m, aryl-H); 7.3- 7.4 (3H, m, aryl-H).

Reference： [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 65

32
[ 31964-56-4 ]
[ 88196-70-7 ]
(R)-N-(1-(3-methoxyphenyl)ethyl)-N-(4-methoxy-3-(3,4-dimethoxyphenyl)phenylmethyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from [4-METHOXY-3- (3,] 4-dimethoxyphenyl) - benzenecarboxaldehyde and [(R)-3-METHOXY-?-METHYLBENZYLAMINE ] according to general procedure C. [C25H29NO4] Mass (calculated): [407]; (found): [[M+H]] = 408. NMR (400 MHz, [CDCL3)] : 1.3 (3H, t, [J = 6 HZ, NCHCH3)] ; 3.55 and 3.6 (2H, dd, [J=12] Hz, CH2N) ; 3.7 and 3.72 (6H, 2 s, 2 CH30) ; 3.8-3. 9 (4H, m, [NCHME] and CH30) ; 6. [8] [(1H,] dd, [J=] 2 and [8] Hz, aryl-H); 6.8-6. 9 (2H, m, aryl-H); 6.9-7 (2H, m, aryl-H); 7-7.05 (2H, m, aryl-H) ; 7.15-7. 3 (3H, m, aryl-H).

Reference： [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 73-74

33
[ 628711-22-8 ]
[ 88196-70-7 ]
(R)-N-(1-(3-methoxyphenyl)ethyl)-N-(4-methoxy-3-(pyrid-2-yl)phenylmethyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from [4-METHOXY-3- (PYRID-2-YL)] benzenecarbox- aldehyde and [(R)-3-METHOXY-OC-METHYLBENZYLAMINE] according to general procedure [C.] [C22H24N202] Mass (calculated): [348]; (found): [[M+H+]] = 349,198. NMR (400 MHz, CDC13) : 1.3 (3H, d, J = 6 Hz, NCHCH3) ; 3.55 and 3.6 [(2H,] dd, [J] = 12 [HZ, CH2N)] ; 3.7-3. 8 (7H, m, 2 MeO and [NCHME)] ; 6.7 [(1H,] dd, J = 1 and 8 Hz, aryl-H); 6. [8-6.] 9 (3H, m, aryl-H); 7.05-7. 3 (3H, m, aryl-H); 7.55-7. 65 (2H, m, aryl-H); 7.75 [(1H,] d, J = 8 Hz, aryl-H); 7.7 [(1H,] d, J = 8 Hz, aryl-H); 8.6 [(1H,] m, pyridyl-H).

Reference： [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 76

34
[ 628711-32-0 ]
[ 88196-70-7 ]
[(1R)-1-(3-methoxyphenyl)ethyl][4-methoxy-3-(1-methylindol-5-yl)phenyl]methyl}amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from 3-(1-methylindol-5-yl)-4-methoxybenz- aldehyde and [(R)-3-METHOXY-OC-METHYLBENZYLAMINE] according to general procedure C. [C26H28N202] Mass (calculated): [400]; (found): [[M+H+]] = 401. NMR (400 MHz, [CDC13)] : 1.3 (3H, d, [J =] 6 Hz, NCHCH3) ; 3.55 and 3.6 (2H, dd, J = 12 Hz, CH2N); 3.65-3. [8] (10H, m, 3 MeO and [NCHME)] ; 6.4 [(1H,] d, [J =] 5 Hz, indole-H); 6.7 [(1H,] dd, [J= 1] and 8 Hz, aryl-H); 6.8-6. 9 (3H, m, aryl-H); 6.95 [(1H,] d, J = 2 Hz, aryl-H); 7.1-7. 3 (4H, m, aryl-H); 7. 35 [(1H,] dd, [J= 1] and 8 Hz, aryl- H); 7.65 [(1H,] d, J = 1 Hz, aryl-H).

Reference： [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 82

35
[ 628711-36-4 ]
[ 88196-70-7 ]
(R)-N-(1-(3-methoxyphenyl)ethyl)-N-(4-methoxy-3-(3-methoxyphenyl)phenylmethyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from 4-methoxy-3- (3-methoxyphenyl) benzene- carboxaldehyde and (R)-3-methoxy-a-methylbenzylamine according to general procedure C. [C24H27NO3] Mass (calculated): [377]; (found): [M+H+] = 378. NMR (400 MHz, CDC13) : 1.4 (3H, d, J = 6 Hz, NCHCH3) ; 3.6 and 3.65 (2H, dd, [J] = 12 Hz, CH2N); 3.8-3. 9 (10H, 3 s and m, [NCHME] and 3 [MEO)] ; 6.8 [(1H,] dd, [J =] 1 and 8 Hz, aryl-H); 6.9 [(1H,] dd, [J = 1] and [8] Hz, aryl-H); 6.95-7 (3H, m, aryl-H); 7.1-7. 2 (2H, m, aryl-H); 7.2-7. 4 (4H, m, aryl-H).

Reference： [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 84-85

36
[ 628711-49-9 ]
[ 88196-70-7 ]
(R)-N-(1-(3-methoxyphenyl)ethyl)-N-(4-cyclopropylmethoxy-3-(4'-methoxyphenyl)phenylmethyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from [4-CYCLOPROPYLMETHOXY-3- (4'-METHOXY-] phenyl) benzenecarboxaldehyde and (R)-3-methoxy-a-methylbenzylamine according to general procedure A. [C27H3IN03] Mass (calculated): [417]; (found): [[M+H+]] = 267,418. NMR (400 MHz, CDCl3) : 0.2 (2H, m, cyclopropyl-H); 0.45 (2H, m, cyclopropyl- H); 1.1 [(1H,] m, cyclopropyl-H); 1.3 (3H, d, J = 6 Hz, NCHCH3) ; 3.5 and 3.55 (2H, dd, [J =] 12 Hz, CH2N) ; 3.65 (2H, d, J = 6 Hz, [CYCLOPROPYLCH20)] ; 3.7 (3H, s, CH30) ; 3.75-3. 85 (4H, m, MeO and [NCHME)] ; 6.75 [(1H,] dd, [J =] 1 and 8 Hz, aryl- H); 6.8 [(1H,] d, [J=] 8 Hz, aryl-H); 6.85-6. 95 (4H, m, aryl-H) ; 7.1 [(1H,] dd, [J= 1] and 8 Hz, aryl-H); 7.15 [(1H,] d, [J=] 1 Hz, aryl-H); 7.15-7. 25 [(1H,] m, aryl-H); 7.45 [(2H,] d, [J = 8 HZ,] aryl-H).

Reference： [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 93

37
[ 628710-56-5 ]
[ 88196-70-7 ]
(R)-N-(1-(3-methoxyphenyl)ethyl)-N-(4-acetamido-3-(4-methoxyphenyl)phenylmethyl)amine [ No CAS ]

Reference： [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 31

38
[ 628710-60-1 ]
[ 88196-70-7 ]
(R)-N-(1-(3-methoxyphenyl)ethyl)-N-(4-methoxy-3-(1-methylbenzimidazo1-5-yl)phenylmethyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from 4-methoxy-3- (1-methylbenzimidazol-5- yl) benzaldehyde and [(R)-3-METHOXY-?-METHYLBENZYLAMINE ] according to general procedure C. [C25H27N302] Mass (calculated): [401]; (found): [[M+H]] = 402,251, 268. NMR (400 MHz, CDC13) : 1.3 (3H, d, J = 6 Hz, NCHCH3) ; 3.55 and 3.6 (2H, dd, [J] = 12 Hz, [CH2N)] ; 3.7-3. 9 (10H, m [AND 2S, NCHME,] NMe and [MEO)] ; 6.7 [(1H,] dd, [J=] 1 and 8 Hz, aryl-H); 6. [85-6.] 95 (3H, m, aryl-H); 7.15-7. 3 (3H, m, aryl-H); 7.35 [(1H,] m, aryl-H); 7.45 [(1H,] m, aryl-H); 7. [8-7.] 95 (2H, m, aryl-H).

Reference： [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 36

39
3-(2H-benzo [d]1,3-dioxolan-5-yl)-4-methoxybenzaldehyde [ No CAS ]
[ 88196-70-7 ]
(R)-N-(1-(3-methoxyphenyl)ethyl)-N-(4-methoxy-3-(4,5-methylendioxyphenyl)phenylmethyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from 3- (2H-benzo [d] 1, 3-dioxolan-5-yl) -4- methoxybenzaldehyde and [(R)-3-METHOXY-OC-METHYLBENZYLAMINE] according to general procedure B. [C24H25NO4] Mass (calculated): [391]; (found): [M+H+] = 392. NMR (400 MHz, CDCl3) : 1.35 (3H, d, [J= 6.] 8 Hz, NCHCH3) ; 3.4-3. [8] (9H, m, OCH3, [OCH3,] CHCH3, CH2N) ; 5.9 (2H, s, OCH2O) ; 6.7-7 (8H, m, aryl-H) ; 7.1-7. 2 (2H, m, aryl- H).

Reference： [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 47

40
[ 628710-83-8 ]
[ 88196-70-7 ]
(R)-N-(1-(3-methoxyphenyl)ethyl)-N-(4-trifluoromethoxy-3-(pyrid-3-yl)phenylmethyl)amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		The title compound was prepared from 4-trifluoromethoxy-3-(pyrid-3- yl) benzenecarboxaldehyde and [(R)-3-METHOXY-OC-METHYLBENZYLAMINE] according to general procedure C. [C22H2LP3N202MASS] (calculated): [402]; (found): [[M+H+]] = 403 NMR (400 MHz, CDC13) : 1.3 (3H, d, J = 6 [HZ, NCHCH3)] ; 3.6 (2H, m, CH2N) ; 3.7-3. 8 (4H, m, [NCHME] and CH30) ; 6.7 [(1H,] dd, J = 1 and 8 Hz, aryl-H) ; 6. [8-6.] 9 (2H, m, aryl- H); 7.20-7. 40 [(5H,] m, [ARYL-H)] ; 7.7 [(1H,] dt, [J=] 1 and 8 Hz, aryl-H); 8.55 [(1H,] d, [J] = 3 Hz, aryl-H); 8.65 [(1H,] bs, aryl-H).

Reference： [1]Patent: WO2003/99776,2003,A1 .Location in patent: Page 49

41
[ 269410-22-2 ]
[ 88196-70-7 ]
2-methoxy-4-(6-[(1R)-1-(3-methoxyphenyl)ethyl]amino}pyrazin-2-yl)phenol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
18%	With sodium carbonate;tetrakis(triphenylphosphine) palladium(0);	In a procedure analogous to Example 2, [REACTION OF 2-(R-?-METHYL-3-METHOXY-] [BENZYLAMINO)-6-CHLORO-PYRAZINE] [(137-2MG,] 0. [52MMOL)] and [2-METHOXY-4-] (4,4, 5, 5- tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (143mg, 0.57mmol) furnished the product (32mg, [18%).] [1H-N.M.R. (CDCL3) No. 1.61 (D, J=6.6HZ, 3H, CH3), ] 3. 79 [(S,] 3H, [OCH3),] 3.94 (s, 3H, OCH3), 4.94 (m, 1H, CH), 5.02 (d, J=6Hz, 1H, NH), 6. 04 (br s, 1H, OH), 6.77-7.48 (m 7H, Ar-H), [7.] 69 (s, 1H, [PYRAZ-H),] 8.23 (s, 1H, [PYRAZ-H)] m/z (ES) 352 (M++H).

Reference： [1]Patent: WO2003/99796,2003,A1 .Location in patent: Page 24-25

42
[ 32315-10-9 ]
[ 88196-70-7 ]
N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-[(1R)-1-(3-methoxyphenyl)ethyl]urea [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47%		Example 50: N-{4-[(6,7-Dimethoxy-4-quinolyl)oxy]phenyl}-N'-[(1R)-1-(3-methoxyphenyl)ethyl]urea 4-[(6,7-Dimethoxy-4-quinolyl)oxy]aniline (70 mg) was dissolved in chloroform (1 ml) and triethylamine (0.1 ml) to prepare a solution. A solution of triphosgene (33 mg) in chloroform (0.2 ml) was then added to the solution, and the mixture was stirred at room temperature for 75 min. Next, a solution of (1R)-1-(3-methoxyphenyl)ethylamine (35 mg) in chloroform (0.2 ml) was added thereto, and the mixture was stirred at room temperature for 10 hr. The stirred mixture was purified by chromatography on silica gel using chloroform/methanol for development to give the title compound (53 mg, yield 47%). 1H-NMR (CDCl3): 1.46 (3H, d, J = 6.83 Hz), 3.75 (3H, s), 4.00 (3H, s), 4.03 (3H, s), 4.95 (1H, m), 5.59 (1H, d, J = 7.07 Hz), 6.40 (1H, d, J = 5.37 Hz), 6.77 (1H, dd, J = 7.81, 2.20 Hz), 6.88 (1H, d, J = 2.20 Hz), 6.91 (1H, d, J = 7.81 Hz), 7.05 (2H, d, J = 8.78 Hz), 7.23 (1H, t, J = 7.81 Hz), 7.28 (1H, s), 7.36 (2H, d, J = 8.78 Hz), 7.39 (1H, s), 7.54 (1H, s), 8.43 (1H, d, J = 5.37 Hz)

Reference： [1]Patent: EP1535910,2005,A1 .Location in patent: Page/Page column 36

43
[ 898545-59-0 ]
[ 88196-70-7 ]
3-(4-hydroxy-3-methyl-phenylamino)-4-[(R)-1-(3-methoxy-phenyl)-ethylamino]-cyclobut-3-ene-1,2-dione [ No CAS ]

Reference： [1]Patent: WO2006/72354,2006,A1 .Location in patent: Page/Page column 32

Yield	Reaction Conditions	Operation in experiment
97%	With aluminum (III) chloride; methoxybenzene; In dichloromethane; at 30℃; for 2h;	General procedure: (3) 1.84 g of compound a-3 was dissolved in 50 mL of dichloromethane,2.18 g of aluminum trichloride and 0.96 g of anisole were added.The mixture was stirred and stirred at 30 C for 2 h to remove the tert-butylsulfonyl group.Washed with water, extracted with dichloromethane,Evaporating the solvent to give 0.91 g of compound a-4, yield 98.40%;
5.8 g (83%)		C. (R)-3-methoxy-alpha-methylbenzylamine A solution of 14.0 g (92.0 mmol) of (R)-(-)-mandelic acid (Aldrich, 99+%), 14.0 g (92.7 mmol) of (+-) 3-methoxy-alpha-methylbenzylamine and 500 mL of isopropanol was brought to reflux and gravity filtered while hot. The solution was then seeded at 50 C. with diastereomerically-pure seeds. After cooling to room temperature, the mixture was filtered to afford 10.9 g of a fluffy, white solid. This was recrystallized from 500 mL of isopropanol. The solids were collected then partitioned between ethyl acetate and saturated Na2 CO3. The organics were washed with saturated NaCl, dried with Na2 SO4, and concentrated to afford 5.8 g (83%) of a yellow oil. NMR analysis of the derived camphorsulfonamide (FIG. 6) indicated that the chemical is enantiomerically pure, to the limits of detection of NMR. This oil was distilled, b.p. 118-120 C. at aspirator pressure, [alpha]D =3.8 (c+1 in 2N HCl).

45
[ 1120-71-4 ]
[ 88196-70-7 ]
3-[(1R)-1-(3-methoxyphenyl)ethyl]amino}propane-1-sulfonic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
91%	In toluene; acetonitrile; for 4h;Heating / reflux;Product distribution / selectivity;	Preparation of (R)-3-[1-(3-methoxyphenyl)ethyl]amino}-1-propanesulfonic acid (Compound QA); To a solution of(1R)-(-)-1-(3-methoxyphenyl)ethylamine (5.0 g, 33.1 mmol) in acetonitrile (30 mL) and toluene (10 mL) was added 1,3-propane sultone (3.85 g, 31.5 mmol). The solution was stirred at reflux for 4 hours. The reaction mixture was cooled to room temperature. The solid material was collected by filtration and washed with acetone (2×20 mL). The solid was suspended in EtOH (40 mL). The suspension was stirred at reflux for 1 hour. The mixture was cooled to room temperature, the solid material was collected by filtration, washed with acetone (2×20 mL) and dried in a vacuum oven at 50 C., affording the title compound, 7.98 g (91%). 1H NMR (D2O, 500 MHz) delta ppm 7.298 (td, 1H, J=1.0 Hz, 7.8 Hz), 6.92 (m, 3H), 4.23 (q, 1H, J=6.8 Hz), 3.69 (s, 3H), 2.95 (m, 1H), 2.78 (m, 3H), 1.92 (m, 2H), 1.50 (d, 3H, J=6.8 Hz). 13C (D2O, 125 MHz) delta ppm 159.69, 137.59, 130.99, 120.23, 115.36, 113.38, 58.53, 55.64, 48.08, 44.50, 21.52, 18.42. [alpha]D=+23.7 (c=0.0036 in water), ES-MS 272 (M-1).

Reference： [1]Patent: US2006/223855,2006,A1 .Location in patent: Page/Page column 164

46
3-benzoylamino-5-(2-ethoxy-3,4-dioxo-cyclobut-1-enylamino)-indazole-1-carboxylic acid tert-butyl ester [ No CAS ]
[ 88196-70-7 ]
3-benzoylamino-5-{2-[(R)-1-(3-methoxyphenyl)-ethylamino]-3,4-dioxo-cyclobut-1-enylamino}-indazole-1-carboxylic acid tert-butyl ester [ No CAS ]

Reference： [1]Patent: WO2006/105865,2006,A1 .Location in patent: Page/Page column 63-64

47
[ 24424-99-5 ]
[ 88196-70-7 ]
[ 266369-69-1 ]

Yield	Reaction Conditions	Operation in experiment
87%	With boron tribromide; triethylamine; In tetrahydrofuran; methanol; dichloromethane;	(1) A dichloromethane (50 ml) solution of boron tribromide (19 ml, 200 mmols) was dropwise added to a dichloromethane (100 ml) solution of <strong>[88196-70-7](R)-1-(3-methoxyphenyl)ethylamine</strong> (10 g, 66 mmols) at -78C. This was stirred at the temperature for 30 minutes, and then reacted at room temperature for 1 hour. Methanol was added to the reaction mixture to stop the reaction, and then the mixturewas concentrated under reduced pressure. To the residue, added were tetrahydrofuran (200 ml), triethylamine (33.8 g, 330 ml) and di-tert-butyl dicarbonate (14.5 g, 66mmols). The resulting mixture was heated under reflux for 2 hours. This was cooled, then poured into water, and extracted with ethyl acetate. The extract was washed with 1 N hydrochloric acid, and brine, and then dried with anhydrous magnesium sulfate. This was concentrated under reduced pressure, and the residue was purified through silica gel column chromatography. An oil of tert-butyl (1R)-1-(3-hydroxyphenyl) ethylcarbamate (13.7 g, 87 %) was obtained. 1H-NMR (CDCl3) delta: 1.42(9H,s), 1.46(3H,s), 4.71(1H,m),

Reference： [1]Patent: EP1123918,2001,A1

48
(R)-N-[3-(2-methylphenyl)prop-2-enyl]-1-(3-methoxyphenyl)ethylamine [ No CAS ]
[ 88196-70-7 ]
(R)-N-[3-(2,4,6-trimethylphenyl)prop-2-enyl]-1-(3-methoxyphenyl)ethylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diisobutylaluminium hydride;	Preparation of 12D In a similar fashion, 2,4,6-trimethylcinnamonitrile was treated with diisobutyl aluminum hydride and the intermediate aluminum-imine complex treated with <strong>[88196-70-7](R)-1-(3-methoxyphenyl)ethylamine</strong>. The intermediate imine was treated with ethanolic sodium borohydride. Work-up and chromatography yielded (R)-N-[3-(2,4,6-trimethylphenyl)prop-2-enyl]-1-(3-methoxyphenyl)ethylamine, 12D, as a clear, colorless oil; m/z (rel. int.) 309 (M+, 8), 294 (25), 174 (82), 159 (100), 135 (52), 129 (29), 105 (21), 91 (17), 77 (14).

Reference： [1]Patent: US6211244,2001,B1

49
(R)-N-[3-(3-methylphenyl)prop-2-enyl]-1-(3-methoxyphenyl)ethylamine [ No CAS ]
[ 88196-70-7 ]
(R)-N-(3-phenylprop-2-enyl)-1-(3-methoxyphenyl)ethylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diisobutylaluminium hydride;	Preparation of 25E In a similar fashion, cinnamonitrile was treated with diisobutyl aluminum hydride and the intermediate aluminum-imine complex treated with <strong>[88196-70-7](R)-1-(3-methoxyphenyl)ethylamine</strong>. The intermediate imine was treated with ethanolic sodium borohydride. Work-up and chromatography yielded (R)-N-(3-phenylprop-2-enyl)-1-(3-methoxyphenyl)ethylamine, 25E, as a clear colorless oil; m/z (rel. int.) 267 (M+. 3), 252 (14),176 (17), 135 (62),117 (100), 105 (28), 91 (56), 77 (33).

Reference： [1]Patent: US6211244,2001,B1

50
(R)-N-(3-phenylprop-2-enyl)-1-(3-methoxyphenyl)ethylamine [ No CAS ]
[ 88196-70-7 ]
(R)-N-(2-methyl-3-phenylprop-2-enyl)-1-(3-methoxyphenyl)ethylamine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With diisobutylaluminium hydride;	Preparation of 25G In a similar fashion, alpha-methylcinnamonitrile was treated with diisobutyl aluminum hydride and the intermediate aluminum-imine complex treated with <strong>[88196-70-7](R)-1-(3-methoxyphenyl)ethylamine</strong>. The intermediate imine was treated with ethanolic sodium borohydride. Work-up and chromatography yielded (R)-N-(2-methyl-3-phenylprop-2-enyl)-1-(3-methoxyphenyl)ethylamine, 25G, as a clear, colorless oil; m/z (rel. int.) 281 (M+, 5), 266 (18), 190 (12), 146 (78), 135 (82), 131 (100), 115 (21), 105 (21), 91 (62), 77 (19).

Reference： [1]Patent: US6211244,2001,B1

51
[ 1694-92-4 ]
[ 88196-70-7 ]
[ 915390-30-6 ]

Reference： [1]Patent: WO2006/123725,2006,A1 .Location in patent: Page/Page column 56

52
[ 1006592-89-7 ]
[ 88196-70-7 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 745 - 748

53
[ 88196-70-7 ]
[ 120681-06-3 ]
[ 1006592-90-0 ]

Reference： [1]Journal of Organic Chemistry,2008,vol. 73,p. 745 - 748

54
[ 90-02-8 ]
[ 88196-70-7 ]
[ 1023279-75-5 ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,2007,vol. 62,p. 807 - 817

55
[ 88196-70-7 ]
[ 50919-07-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In dimethyl sulfoxide; at 90℃; for 2.25h;Product distribution / selectivity;	EXAMPLE 7: CONVERSION OF R- (-)-[1-(3-METHOXYPHENYL) ETHYL] DIMETHYL AMINE INTO ITS RACEMIC MIXTURE OF FORMULA VI; 100 g of R-(-)-[1-(3-methoxyphenyl) ethyl] dimethyl amine mandelic acid salt, 500 ml water was charged and stirred for about 15 minutes. pH of the reaction solution was a adjusted to 10 by addition of 40% aqueous sodium hydroxide solution and stirred for about 20 minutes. 500 ml ethyl acetate was added to the reaction solution and stirred for about 10 minutes and separated the organic and aqueous layer. The obtained organic layer was distilled off completely under vacuum to get 48.8 g of the residue 2 g of the above obtained residue containing R-(-)-[1-(3-methoxyphenyl) ethyl] dimethyl amine, 0.5 g of sodium hydroxide and 10 ml of dimethyl sulfoxide were charged in a clean and dry round bottom flask and stirred for about 15 minutes. The reaction mixture was heated to about 90C and maintained for about 2 hours followed by cooling to room temperature. 50 ml of water were added to the above reaction mixture and stirred for about 45 minutes. To the resultant reaction solution 15 ml dichloromethane was added and stirred for about 15 minutes and separated the organic layer. The obtained organic layer was distilled off completely under vacuum below 45 to 1.3 g of 1-(3-methoxyphenyl) ethyl] dimethyl amine of Formula VI. Entiomeric ratio by chiral HPLC: 49.93:50.07
	With sodium hydroxide; In dimethyl sulfoxide; at 90℃; for 2.25h;Product distribution / selectivity;	Example 7; Conversion of R-(-)-[1-(3-Methoxyphenyl) Ethyl] Dimethyl Amine into its Racemic Mixture of Formula VI; 100 g of R- (-)-[1-(3-methoxyphenyl)ethyl] dimethyl amine mandelic acid salt, 500 ml water was charged and stirred for about 15 minutes. pH of the reaction solution was a adjusted to 10 by addition of 40% aqueous sodium hydroxide solution and stirred for about 20 minutes. 500 ml ethyl acetate was added to the reaction solution and stirred for about 10 minutes and separated the organic and aqueous layer. The obtained organic layer was distilled off completely under vacuum to get 48.8 g of the residue.2 g of the above obtained residue containing R- (-)-[1-(3-methoxyphenyl)ethyl] dimethyl amine, 0.5 g of sodium hydroxide and 10 ml of dimethyl sulfoxide were charged in a clean and dry round bottom flask and stirred for about 15 minutes. The reaction mixture was heated to about 90 C. and maintained for about 2 hours followed by cooling to room temperature. 50 ml of water were added to the above reaction mixture and stirred for about 45 minutes. To the resultant reaction solution 15 ml dichloromethane was added and stirred for about 15 minutes and separated the organic layer. The obtained organic layer was distilled off completely under vacuum below 45 to 1.3 g of 1-(3-methoxyphenyl)ethyl] dimethyl amine of Formula VI.Entiomeric ratio by chiral HPLC: 49.93:50.07

Reference： [1]Patent: EP1980552,2008,A2 .Location in patent: Page/Page column 12
[2]Patent: US2008/255383,2008,A1 .Location in patent: Page/Page column 7

56
[ 186660-13-9 ]
[ 88196-70-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; water; for 0.333333h;pH 10.0;	EXAMPLE 7: CONVERSION OF R- (-)-[1-(3-METHOXYPHENYL) ETHYL] DIMETHYL AMINE INTO ITS RACEMIC MIXTURE OF FORMULA VI; 100 g of R-(-)-[1-(3-methoxyphenyl) ethyl] dimethyl amine mandelic acid salt, 500 ml water was charged and stirred for about 15 minutes. pH of the reaction solution was a adjusted to 10 by addition of 40% aqueous sodium hydroxide solution and stirred for about 20 minutes. 500 ml ethyl acetate was added to the reaction solution and stirred for about 10 minutes and separated the organic and aqueous layer. The obtained organic layer was distilled off completely under vacuum to get 48.8 g of the residue 2 g of the above obtained residue containing R-(-)-[1-(3-methoxyphenyl) ethyl] dimethyl amine, 0.5 g of sodium hydroxide and 10 ml of dimethyl sulfoxide were charged in a clean and dry round bottom flask and stirred for about 15 minutes. The reaction mixture was heated to about 90C and maintained for about 2 hours followed by cooling to room temperature. 50 ml of water were added to the above reaction mixture and stirred for about 45 minutes. To the resultant reaction solution 15 ml dichloromethane was added and stirred for about 15 minutes and separated the organic layer. The obtained organic layer was distilled off completely under vacuum below 45 to 1.3 g of 1-(3-methoxyphenyl) ethyl] dimethyl amine of Formula VI. Entiomeric ratio by chiral HPLC: 49.93:50.07
	With sodium hydroxide; water; for 0.333333h;pH 10.0;	Example 7; Conversion of R-(-)-[1-(3-Methoxyphenyl) Ethyl] Dimethyl Amine into its Racemic Mixture of Formula VI; 100 g of R- (-)-[1-(3-methoxyphenyl)ethyl] dimethyl amine mandelic acid salt, 500 ml water was charged and stirred for about 15 minutes. pH of the reaction solution was a adjusted to 10 by addition of 40% aqueous sodium hydroxide solution and stirred for about 20 minutes. 500 ml ethyl acetate was added to the reaction solution and stirred for about 10 minutes and separated the organic and aqueous layer. The obtained organic layer was distilled off completely under vacuum to get 48.8 g of the residue.2 g of the above obtained residue containing R- (-)-[1-(3-methoxyphenyl)ethyl] dimethyl amine, 0.5 g of sodium hydroxide and 10 ml of dimethyl sulfoxide were charged in a clean and dry round bottom flask and stirred for about 15 minutes. The reaction mixture was heated to about 90 C. and maintained for about 2 hours followed by cooling to room temperature. 50 ml of water were added to the above reaction mixture and stirred for about 45 minutes. To the resultant reaction solution 15 ml dichloromethane was added and stirred for about 15 minutes and separated the organic layer. The obtained organic layer was distilled off completely under vacuum below 45 to 1.3 g of 1-(3-methoxyphenyl)ethyl] dimethyl amine of Formula VI.Entiomeric ratio by chiral HPLC: 49.93:50.07

Reference： [1]Patent: EP1980552,2008,A2 .Location in patent: Page/Page column 12
[2]Patent: US2008/255383,2008,A1 .Location in patent: Page/Page column 7

57
[ 824-79-3 ]
[ 79-04-9 ]
[ 88196-70-7 ]
[ 1085449-72-4 ]

Reference： [1]Tetrahedron,2008,vol. 64,p. 10350 - 10354

58
[ 88196-70-7 ]
[ 586-37-8 ]
C₁₈H₂₁NO₂ [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 1287 - 1290

59
[ 88196-70-7 ]
4-chloro-1-methyl-1H-pyrazole-3-carbaldehyde [ No CAS ]
C₁₄H₁₆ClN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; at 20℃;	Example 2; The compounds shown in Table 3 below were prepared by the following general procedure.; H2N R2T 2Me; To a solution of aldehyde 1 (0.5 mmol) in MeOH (0.75 mL) was added a solution of amine 2 (0.6 mmol) in MeOH (0.75 mL). The reaction mixture was shaken at room temperature overnight. Amberlite IRA -400 supported borohydride (1 mmol) was added and the reaction mixture was shaken overnight at room temperature. DCM (1 mL) and Wang- aldehyde resin (4-benzyloxybenzaldehyde, polymer-bound; 0.2 mmol) were added and the reaction mixture was shaken overnight at room temperature. The resins were filtered off and <n="31"/>washed with THF (3 x 0.5 mL). The solvents were evaporated under reduced pressure to give amine 3.

Reference： [1]Patent: WO2009/51718,2009,A2 .Location in patent: Page/Page column 29-30

60
[ 50919-07-8 ]
[ 141-78-6 ]
[ 50919-07-8 ]
[ 88196-70-7 ]
(R)-N-acetyl-1-(3-methoxyphenyl)ethylamine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2009,vol. 74,p. 5304 - 5310

61
C₁₂H₁₃N₃ [ No CAS ]
[ 32315-10-9 ]
[ 88196-70-7 ]
[ 1207612-50-7 ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of (R)-1-(3-methoxyphenyl)ethanamine (71.5 mg, 0.473 mmol), triethylamine (0.081 mL, 0.58 mmol), and triphosgene (48.5 mg, 0.163 mmol) in dichloromethane (1.5 mL) was stirred 2 h at room temperature, and added to a mixture of the product from Step A, triethylamine (0.08 mL, 0.6 mmol), and N,N-dimethylformamide (2 mL). The resulting mixture was stirred overnight at room temperature, diluted with ethyl acetate, washed with water and brine, dried (Na2SO4), filtered, concentrated, and chromatographed (25% acetone/dichloromethane) to give 36 mg the title compound as a white solid (36 mg, 0.096 mmol). 1H NMR (300 MHz, DMSO-d6) delta ppm 11.66 (bs, 1H), 8.17 (d, J=4.8 Hz, 1H), 7.47 (t, J=2.8 Hz, 1H), 7.21 (t, J=7.9 Hz, 1H), 6.99 (d, J=5.2 Hz, 1H), 6.89-6.94 (m, 2H), 6.72-6.84 (m, 2H), 6.61 (dd, J=2.0, 3.6 Hz, 1H), 6.37 (bs, 1H), 4.85 (quin, J=7.1 Hz, 1H), 4.08-4.14 (m, 2H), 3.73 (s, 3H), 3.61 (t, J=5.6 Hz, 2H), 2.57 (bs, 2H), 1.38 (d, J=7.1 Hz, 3H); MS (ESI+) M/Z 377.0 (M+H)+.

Reference： [1]Patent: US2010/35919,2010,A1 .Location in patent: Page/Page column 32

62
C₂₅H₃₄N₂O₃ [ No CAS ]
[ 88196-70-7 ]
[ 1187776-91-5 ]
C₃₄H₄₇N₃O₃ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4781 - 4785

63
[ 1234693-05-0 ]
[ 88196-70-7 ]

Reference： [1]Tetrahedron Letters,2010,vol. 51,p. 3536 - 3537

64
[ 5750-76-5 ]
[ 88196-70-7 ]
[ 1236130-71-4 ]

Yield	Reaction Conditions	Operation in experiment
95%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 48h;	Step A: 2,5-Dichloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]pyrimidin-4-amine To a solution of (1R)-1-(3-methoxyphenyl)ethanamine (1.50 g, 9.92 mol) (R-isomer, >98% ee purity) and 2,4,5-trichloropyrimidine (1.19 mL, 10.4 mmol) in N,N-dimethylformamide (30 mL) was added potassium carbonate (4.1 g, 30 mmol). The resultant mixture was stirred over two days at room temperature. The reaction was quenched with water. EtOAc was added and the layers were separated. The aqueous layer was extracted with EtOAc twice. The combined organic layers were washed with water and brine successively, then dried (Na2SO4), filtered, concentrated, and triturated with cold EtOAc to give the desired product as a light yellow gel (2.81 g, 95%). LCMS for C13H14Cl2N3O (M+H)+: m/z=298.0.

Reference： [1]Patent: US2010/190804,2010,A1 .Location in patent: Page/Page column 67

65
[ 108-24-7 ]
[ 88196-70-7 ]
(R)-N-acetyl-1-(3-methoxyphenyl)ethylamine [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 5500 - 5502
[2]Journal of Organic Chemistry,2013,vol. 78,p. 5314 - 5327
[3]Green Chemistry,2017,vol. 19,p. 474 - 480
[4]Journal of the American Chemical Society,2018,vol. 140,p. 2024 - 2027

66
[ 83220-73-9 ]
[ 88196-70-7 ]
[ 870859-03-3 ]

Yield	Reaction Conditions	Operation in experiment
		(1) To a solution of 25 g of tert-butyl (S)-3-hydroxy-pyrrolidine-1-carboxylate and 25.9 g of diisopropylethylamine dissolved in 500 ml of methylene chloride was added dropwise 100 ml of a solution of 49 g of anhydrous trifluoromethanesulfonic acid in methylene chloride at - 20C or lower. The reaction mixture was stirred for 15 minutes while maintaining it to -20C, and then, to the mixture was added dropwise 100 ml of a solution of 24.2 g of <strong>[88196-70-7](R)-1-(3-methoxyphenyl)ethylamine</strong> in methylene chloride at -20C or lower, and the reaction mixture was stirred at room temperature for 16 hours. To the reaction mixture were added a saturated aqueous sodium bicarbonate solution and chloroform, the mixture was stirred and the liquids were separated. The organic layer was dried and the solvent was evaporated, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate= 2:1?1:2) to obtain 19.32 g of tert-butyl 3-[(R)-1-(3-methoxyphenyl)ethylamino]pyrrolidine-1-carboxylate.

Reference： [1]Patent: EP1757582,2007,A1 .Location in patent: Page/Page column 32-33

67
[ 101385-90-4 ]
[ 88196-70-7 ]
[ 870859-01-1 ]

Yield	Reaction Conditions	Operation in experiment
		(1) To a solution of 8.0 g of (R)-1-benzyl-3-pyrrolidinol and 16.5 ml of diisopropylethylamine dissolved in 400 ml of methylene chloride was added dropwise a solution of 13.4 g of anhydrous trifluoromethanesulfonic acid in 50 ml of a methylene chloride at -20C or lower. The reaction mixture was stirred for 15 minutes while maintaining it to -20C, then, a solution of 9.88 g of (R)-1-(3-methoxyphenyl)-ethylamine in 100 ml of methylene chloride was added dropwise to the mixture at -20C or lower, and the reaction mixture was stirred at room temperature for 16 hours. To the reaction mixture were added a saturated aqueous sodium bicarbonate solution and chloroform, the mixture was stirred and the liquids were separated. The organic layer was dried and concentrated, and the residue was purified by silica gel column chromatography (chloroform:methanol=1:0? 50:1) and NH silica gel column chromatography (hexane:ethyl acetate=25:1?10:1) to obtain 3.98 g of (S)-(1-benzyl-pyrrolidin-3-yl)-[(R)-1-(3-methoxyphenyl)ethyl]amine. MS · APCI (m/z): 311 [M+H] +

Reference： [1]Patent: EP1757582,2007,A1 .Location in patent: Page/Page column 32

68
C₁₂H₁₅NO₃S [ No CAS ]
[ 88196-70-7 ]
[ 1257104-30-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium tris(acetoxy)borohydride; acetic acid; In 1,2-dichloro-ethane; at 20℃;	General procedure ETo a solution of 2-cyclopenten-l-one (400 mumol) in 400 mul_ DME were added boronic acid (480 mumol, 1.2 eq.), (COD)Rh(l,4-dihydroquinone)BF4 (1 mol%) in 100 muL DME, and LiOH (4 mol%) in 600 muL water. After shaking the mixture overnight at 50 0C, the solvent was removed in vacuo. The crude intermediate ketone was dissolved in DCE containing acetic acid (1.2 eq.). An amine (1 eq.) in DCE was added followed by NaBH(OAc)3 (1.2 eq.) The mixture was shaken overnight at r. t., filtered and the solvents were removed in vacuo. The residue was redissolved in 750 muL DMSO and purified by preparative HPLC-MS.; Example 55. (lR)-(N)-[(lR/S,3R/S)-3-[4-acetamidophenyl]cyclopentyl]-l-(3- methoxyphenyl)ethanamine (mixture of stereoisomers) (compound 1054)General procedure E was followed using (4-acetylaminophenyl)boronic acid as the boronic acid and (R)-l-(3-methoxyphenyl)ethylamine as the amine. LC-MS (method B): RT = 3.99, M = 352.

Reference： [1]Patent: WO2010/136037,2010,A1 .Location in patent: Page/Page column 52; 84

69
[ 55687-02-0 ]
[ 88196-70-7 ]
[ 1257090-13-3 ]

Yield	Reaction Conditions	Operation in experiment
82%	In dimethyl sulfoxide; at 20℃; for 16h;	6-bromo, 2-chloroquinoxaline (0.300 g, 1.2 mmol) was dissolved in DMSO (15 ml.) at room temperature and (R)-1-(3-Methoxy-phenyl)-ethylamine (0.85 g, 6.1 mmol) was added. The reaction mixture was stirred at RT for 16 hours. After completion of the reaction (confirmed by TLC), water (100 mL) was added to the reaction mixture and it was extracted with ethyl acetate (50 mL x 3). The organic layer was washed with water (15 mL), brine (15 mL), and then dried over Na2SO4. The organic layer was concentrated in vacuo to afford crude product. The crude product was adsorbed on silica gel and purified by column chromatography using neutral silica gel of 60-120 mesh size. A gradient of 1-1.5 % methanol in DCM was used to elute the title compound as a solid (0.35 g, 82%).

Reference： [1]Patent: WO2010/136755,2010,A1 .Location in patent: Page/Page column 74; 75

70
[ 42860-10-6 ]
[ 88196-70-7 ]
[ 1252809-16-7 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 5544 - 5547

71
[ 800402-07-7 ]
[ 88196-70-7 ]
C₁₇H₁₆ClN₃O₂ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7107 - 7112

72
[ 101774-27-0 ]
[ 88196-70-7 ]
[ 1296201-94-9 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 7107 - 7112

73
[ 1233707-35-1 ]
[ 50919-07-8 ]
[ 88196-70-7 ]

Reference： [1]Applied Organometallic Chemistry,2011,vol. 25,p. 105 - 109

74
[ 591-31-1 ]
[ 88196-70-7 ]

Reference： [1]Applied Organometallic Chemistry,2011,vol. 25,p. 105 - 109

75
[ 349451-05-4 ]
[ 88196-70-7 ]

Reference： [1]Applied Organometallic Chemistry,2011,vol. 25,p. 105 - 109

76
[ 88196-70-7 ]
[ 708-06-5 ]
[ 1374843-42-1 ]

Reference： [1]Inorganica Chimica Acta,2012,vol. 387,p. 173 - 180

77
[ 98-98-6 ]
[ 88196-70-7 ]
[ 1332481-84-1 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2948 - 2951

78
[ 88196-70-7 ]
[ 1380678-54-5 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2948 - 2951

79
[ 88196-70-7 ]
[ 1380678-78-3 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 2948 - 2951

80
[ 187672-13-5 ]
[ 50919-07-8 ]
[ 88196-70-7 ]

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 716 - 721

81
[ 187672-13-5 ]
[ 88196-70-7 ]

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 716 - 721

82
[ 1384454-55-0 ]
[ 50919-07-8 ]
[ 88196-70-7 ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: At first, borane/THF (25 mL, 25 mmol) was added to a solution of (S)-valinol (1.29 g, 12.5 mmol) in THF (10 mL) at 0 C, and the mixture was stirred for 5 h in an ice-water bath. A solution of 13 (2.55 g, 10 mmol) in THF (10 mL) was then added dropwise and the mixture was stirred for 24 h at room temperature. Next, borane/THF (50 mL, 50 mmol) was added, the mixture was gently refluxed for 24 h, then cooled, acidified with 2 M hydrochloric acid, and stirred for 24 h at room temperature. It was then concentrated under vacuum, alkalized with 20% aqueous sodium hydroxide, and extracted with ethyl acetate (3 × 50 mL). The organic solution was washed with saturated brine (50 mL), and dried over anhydrous magnesium sulfate. The solvent was removed and the product was isolated by flash chromatography, silica gel, dichloromethane-methanol-triethylamine 9:1:0.1, 1.12 g, 74%
		General procedure: At first, borane/THF (25 mL, 25 mmol) was added to a solution of (S)-valinol (1.29 g, 12.5 mmol) in THF (10 mL) at 0 C, and the mixture was stirred for 5 h in an ice-water bath. A solution of 13 (2.55 g, 10 mmol) in THF (10 mL) was then added dropwise and the mixture was stirred for 24 h at room temperature. Next, borane/THF (50 mL, 50 mmol) was added, the mixture was gently refluxed for 24 h, then cooled, acidified with 2 M hydrochloric acid, and stirred for 24 h at room temperature. It was then concentrated under vacuum, alkalized with 20% aqueous sodium hydroxide, and extracted with ethyl acetate (3 × 50 mL). The organic solution was washed with saturated brine (50 mL), and dried over anhydrous magnesium sulfate. The solvent was removed and the product was isolated by flash chromatography, silica gel, dichloromethane-methanol-triethylamine 9:1:0.1, 1.12 g, 74%

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 716 - 721
[2]Tetrahedron Asymmetry,2012,vol. 23,p. 716 - 721

83
[ 1384454-55-0 ]
[ 88196-70-7 ]

Yield	Reaction Conditions	Operation in experiment
71%		General procedure: At first, borane/THF (25 mL, 25 mmol) was added to a solution of (S)-valinol (1.29 g, 12.5 mmol) in THF (10 mL) at 0 C, and the mixture was stirred for 5 h in an ice-water bath. A solution of 13 (2.55 g, 10 mmol) in THF (10 mL) was then added dropwise and the mixture was stirred for 24 h at room temperature. Next, borane/THF (50 mL, 50 mmol) was added, the mixture was gently refluxed for 24 h, then cooled, acidified with 2 M hydrochloric acid, and stirred for 24 h at room temperature. It was then concentrated under vacuum, alkalized with 20% aqueous sodium hydroxide, and extracted with ethyl acetate (3 × 50 mL). The organic solution was washed with saturated brine (50 mL), and dried over anhydrous magnesium sulfate. The solvent was removed and the product was isolated by flash chromatography, silica gel, dichloromethane-methanol-triethylamine 9:1:0.1, 1.12 g, 74%

Reference： [1]Tetrahedron Asymmetry,2012,vol. 23,p. 716 - 721

84
[ 88196-70-7 ]
[ 22244-22-0 ]
[ 1400984-80-6 ]

Yield	Reaction Conditions	Operation in experiment
92.71%		(R)-l-(3-Methoxyphenyl)ethanamine (1.46 g, 0.00966 mol) was taken in dry toluene (10 mL) under nitrogen atmosphere. This solution was heated to 50C and then added trimethyl aluminium (0.65 mL, 0.0072 mol, 2 M solution in toluene). The reaction mixture was stirred for 15 min at the same temperature then slowly added a mixture of Intermediate- la (1 g, 0.0048 mol) in toluene (10 mL). The reaction mixture was heated to 110C and further maintained for 5 h. The progress of the reaction was monitored by TLC. The reaction mixture was quenched with dilute HC1, and the product extracted into ethyl acetate. Organic layer was washed with water followed by brine solution. The organic layers were combined, dried over sodium sulfate and concentrated to get crude compound. Purification was carried out by flash chromatography using a mixture of 15%ethyl acetate in hexane afforded the title compound 1.40 g (92.71 %). m/z 313.2.
92.71%	With trimethylaluminum; In toluene; at 50 - 110℃; for 5.25h;Inert atmosphere;	Intermediate-4 N-((i?)-l-(3-Methoxyphen l)ethyl)-3,4-dihydro-2H-benzo[&][l ,4]oxazine-2-carboxamide (i?)-l-(3-Methoxyphenyl) ethanamine (1.46 g, 0.00966mol) was taken in dry toluene (10 mL) under nitrogen atmosphere. This solution was heated to 50C and then added trimethyl aluminium (0.65mL, 0.0072mol, 2M solution in toluene). The reaction mixture was stirred for 15 min at the same temperature then slowly added a mixture of ethyl 3,4-dihydro-2H- benzo[b][l, 4]oxazine-2-carboxylate (Intermediate- la) (1 g, 0.0048 mol) in toluene (10 mL). The reaction mixture was heated to 110C and maintained for 5 hr. The progress of the reaction was monitored by TLC. The reaction was quenched with dilute HCl and the product extracted into ethyl acetate. Organic layer was washed with water followed by brine solution. The organic layers were combined, dried over sodium sulfate and concentrated to get amide. Purification was carried out by flash chromatography using a mixture of ethyl acetate /hexane afforded the title compound 1.40 g (92.71 %). m/z 313.2.

Reference： [1]Patent: WO2012/127385,2012,A1 .Location in patent: Page/Page column 44
[2]Patent: WO2013/136288,2013,A1 .Location in patent: Page/Page column 28

85
[ 1401076-78-5 ]
[ 88196-70-7 ]
[ 1401074-88-1 ]

Yield	Reaction Conditions	Operation in experiment
52.63%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 100℃; for 22h;	To stirred solution of Intermediate-8 (0.4 g, 0.0945 mmol) in DCM (1 mL), DIPEA (2 mL, 34 mmol) and (R)- l-(3-methoxyphenyl) ethanamine (0.016 g, 0.103 mmol) were added, then heated to 100C and further stirred for 22 h at the same temperature. The progress of reaction was monitored by TLC. The reaction mixture was cooled to room temperature and diluted with ethyl acetate and the organic layer washed with water followed by brine solution. The organic layer was dried over sodium sulfate and concentrated under vacuum to get the crude product. This crude product was further purified by flash chromatography using a mixture of 10% ethyl acetate in hexane (0.4 g, 52.63%).m/z 403.2; *H NMR (400 MHz, CDC13): delta 7.43-7.30 (m, 5H), 7.23-7.17 (m,lH), 6.98.6.95 (m,lH), 6.92-6.90 (m, lH), 6.85 (m,2H), 6.77 (t, 7=8.8 Hz, 2H), 6.6 (m, lH), 4.48 (m,lH), 4.11(m, lH), 3.86 (m, lH), 3.75 (m,6H), 3.69-3.64 (m, 1H), 2.80-2.80 (m,2H), 1.43 (d, J = 6.4 Hz,3H).

Reference： [1]Patent: WO2012/127385,2012,A1 .Location in patent: Page/Page column 66-67

86
[ 2004-06-0 ]
[ 88196-70-7 ]
N⁶-[(R)-1-(3-methoxyphenyl)ethyl]adenosine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In propan-1-ol; at 80℃; for 6h;	A mixture of (R)-1-(3-methoxyphenyl)-ethylamine (635 mg) and 6-chloropurine riboside (300 mg) in PrOH (50 ml) was heated to 80C for 6 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over Sephadex LH-20 gel and eluted with ethanol to yield N6-[(R)-1-(3-methoxyphenyl)-ethyl]-adenosine(335 mg) as a white solid: positive ESIMS mlz 402 [M + H]+; negative ESIMS mlz 400 [M - H]-; 1H NMR (300 MHz, DMSO-d6):the adenosine moietydelta 8.39 (1H, s, H-2), 8.30 (1H, brd, J = 4.8 Hz, -NH), 8.18 (1H, s, H-8), 5.90 (1H, d, J = 6.3 Hz, H-1'), 5.46 (2H, m, 2*-OH), 5.21 (1H, m, -OH), 4.63 (1H, m, H-2'), 4.17 (1H, m, H-3'), 3.98 (1H, m, H-4'), 3.68 (1H, m, H-5'a), 3.58 (1H, m, H-5'b); the (R)-1-(3-methoxyphenyl)-ethyl moiety delta 7.19 (1H, t, J= 7.5Hz, H-5'), 7.03 (1H, brs, H-2'), 7.00 (1H, brd, J = 7.5 Hz, H-6'), 6.74 (1H, dd, J = 7.5, 1.5Hz, H-4'), 5.49 (1H, m, H-7'), 3.70 (3H, s, -OCH3), 1.52 (1H, d, J = 6.6 Hz, H-8'); 13CNMR (75MHz, DMSO-d6): the adenosine moiety delta 153.9 (s, C-6), 152.3 (d, C-2), 148.6 (s, C-4), 139.9 (d, C-8), 119.8 (s, C-5), 88.1 (d, C-1'), 86.0 (d, C-4'), 73.5 (d, C-2'), 70.8 (d, C-3'), 61.8 (t, C-5'); the (R)-1-(3-methoxyphenyl)-ethyl moiety delta 159.3 (s, C-3'), 146.9 (s, C-1'), 129.3 (d, C-5'), 118.5 (d, C-6'), 112.2 (d, C-2'), 111.7 (d, C-4'), 55.0 (q, -OCH3), 48.9 (d, C-7'), 22.6 (q, C-8')o
335 mg	In propan-1-ol; at 80℃; for 6h;	A mixture of (R)-1-(3-methoxyphenyl)-ethylamine (635 mg) and 6-chloropurine riboside (300 mg) in PrOH (50 ml) was heated to 80 C. for 6 h. After evaporation of the reaction mixture, the residue was separated by column chromatography over Sephadex LH-20 gel and eluted with ethanol to yield N6-[(R)-1-(3-methoxyphenyl)-ethyl]-adenosine (335 mg) as a white solid: positive ESIMS m/z 402 [M+H]+; negative ESIMS m/z 400 [M-H]-; 1H NMR (300 MHz, DMSO-d6): the adenosine moiety delta 8.39 (1H, s, H-2), 8.30 (1H, brd, J=4.8 Hz, -NH), 8.18 (1H, s, H-8), 5.90 (1H, d, J=6.3 Hz, H-1'), 5.46 (2H, m, 2*-OH), 5.21 (1H, m, -OH), 4.63 (1H, m, H-2'), 4.17 (1H, m, H-3'), 3.98 (1H, m, H-4'), 3.68 (1H, m, H-5'a), 3.58 (1H, m, H-5'b); the (R)-1-(3-methoxyphenyl)-ethyl moiety delta 7.19 (1H, t, J=7.5 Hz, H-5"), 7.03 (1H, brs, H-2"), 7.00 (1H, brd, J=7.5 Hz, H-6"), 6.74 (1H, dd, J=7.5, 1.5 Hz, H-4"), 5.49 (1H, m, H-7"), 3.70 (3H, s, -OCH3), 1.52 (1H, d, J=6.6 Hz, H-8"); 13CNMR (75 MHz, DMSO-d6): the adenosine moiety delta 153.9 (s, C-6), 152.3 (d, C-2), 148.6 (s, C-4), 139.9 (d, C-8), 119.8 (s, C-5), 88.1 (d, C-1'), 86.0 (d, C-4'), 73.5 (d, C-2'), 70.8 (d, C-3'), 61.8 (t, C-5'); the (R)-1-(3-methoxyphenyl)-ethyl moiety delta 159.3 (s, C-3"), 146.9 (s, C-1"), 129.3 (d, C-5"), 118.5 (d, C-6"), 112.2 (d, C-2"), 111.7 (d, C-4"), 55.0 (q, -OCH3), 48.9 (d, C-7"), 22.6 (q, C-8").
335 mg	In propan-1-ol; at 80℃; for 6h;	(R)-1-(3-methoxyphenyl)-ethylamine (635 mg) was dissolved in normal propyl alcohol (50 mL), 6-chloropurine nucleoside (300 mg) Heat up to 80 C and let it react for 6 h. The solvent was recovered with the reaction solution, chromatographed through a gel column and eluted with ethanol to obtain white solid N6-[(R)-1-(3-methoxyphenyl)-ethyl]-adenosine (335 mg) It was

Reference： [1]Patent: EP2511283,2012,A1 .Location in patent: Page/Page column 73-74
[2]Patent: US2013/45942,2013,A1 .Location in patent: Paragraph 0289; 0290
[3]Patent: JP2015/172077,2015,A .Location in patent: Paragraph 0157

87
[ 5000-65-7 ]
[ 88196-70-7 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 5314 - 5327

88
C₉H₁₀BrNO₂ [ No CAS ]
[ 88196-70-7 ]

Reference： [1]Journal of Organic Chemistry,2013,vol. 78,p. 5314 - 5327

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Precautionary Statements-General
Code	Phrase
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Code	Phrase
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P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 88196-70-7 ] {[proInfo.proName]}

Quality Control of [ 88196-70-7 ]

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Product Details of [ 88196-70-7 ]

Calculated chemistry of [ 88196-70-7 ]

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

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Application In Synthesis of [ 88196-70-7 ]

[ 88196-70-7 ] Synthesis Path-Downstream 1~88

Related Functional Groups of [ 88196-70-7 ]

Aryls

Ethers

Amines

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[ 88196-70-7 ]