[ CAS No. 3554-65-2 ] {[proInfo.proName]}

Name: 3554-65-2|(1-Methylpyrrolidin-2-yl)methanol|97%
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SKU: A199057
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Quality Control of [ 3554-65-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 3554-65-2 ]

Product Details of [ 3554-65-2 ]

CAS No. :	3554-65-2	MDL No. :	MFCD06200823
Formula :	C₆H₁₃NO	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	115.17	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 3554-65-2 ]

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	1
Num. H-bond acceptors :	2.0
Num. H-bond donors :	1.0
Molar Refractivity :	36.81
TPSA :	23.47 Å²

Pharmacokinetics

GI absorption :	Low
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.78
Log Po/w (XLOGP3) :	0.13
Log Po/w (WLOGP) :	-0.31
Log Po/w (MLOGP) :	0.21
Log Po/w (SILICOS-IT) :	0.51
Consensus Log Po/w :	0.46

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.57
Solubility :	31.0 mg/ml ; 0.269 mol/l
Class :	Very soluble
Log S (Ali) :	-0.18
Solubility :	76.3 mg/ml ; 0.662 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.26
Solubility :	63.9 mg/ml ; 0.555 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.48

Safety of [ 3554-65-2 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 3554-65-2 ]

* 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.

Upstream synthesis route of [ 3554-65-2 ]
Downstream synthetic route of [ 3554-65-2 ]

[ 3554-65-2 ] Synthesis Path-Upstream 1~10

1
[ 68078-09-1 ]
[ 3554-65-2 ]
[ 34381-71-0 ]

Reference： [1] Journal of Organic Chemistry, 1995, vol. 60, # 18, p. 5763 - 5769

2
[ 50-00-0 ]
[ 498-63-5 ]
[ 3554-65-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	With hydrogen In water for 18 h;	a) (/?S)-(1 -Methylpyrrolidin-2-yl)methanoIA mixture of (RS)-pyrrolidin-2-ylmethanol (1.00 g, 9.90 mrnol, 1.0 eq), formaldehyde (35percent aqueous, 10 mL) and 10percent Pd/C (200 mg) was stirred under a balloon of hydrogen gas for 18 h. The mixture was filtered through a Celite pad, concentrated under reduced pressure and purification by silica gel chromatography (20percent MeOH/CHCI₃) gave a colorless liquid (650 mg, 56percent); ¹H NMR (400 MHz, CDCI₃) 6 ppm 3.65 (dd, =10.0, 3.6 Hz, 1 H), 3.43 (dd, J=10.8, 2.0 Hz, 1H), 3.10-3.05 (m, 1 H), 2.40-2.35 (m, 1 H), 2.33 (s, 3H), 2.32-2.25 (m, 1 H), 1.93-1.68 (m, 4H); m/z (APCIf: 116 [M+H]⁺.

Reference： [1] Patent: WO2012/127212, 2012, A1, . Location in patent: Page/Page column 101

3
[ 933-94-8 ]
[ 3554-65-2 ]

Yield	Reaction Conditions	Operation in experiment
47.4%	Stage #1: With diisobutylaluminium hydride In dichloromethane for 6 h; Stage #2: With methanol In dichloromethane	Step 3 (1-Methylpyrrolidin-2-yl)methanol Diisobutyl aluminium hydride (60 mL, 66 mmol) was added dropwise to a solution of methyl 1-methylpyrrolidine-2-carboxylate 10c (4.7 g, 33 mmol) in 50 mL of dichloromethane. The reaction mixture was stirred for 6 hours in an ice-water bath, followed by addition of 10 mL of methanol. The reaction mixture was concentrated under reduced pressure to obtain the title compound (1-methylpyrrolidin-2-yl)methanol 10d (1.8 g, yield 47.4percent) as a brown oil.
1.8 g	With diisobutylaluminium hydride In dichloromethane for 6 h; Cooling with ice; Inert atmosphere	Diisobutylaluminum hydride (60 mL, 66 mmol) was added dropwise to 50 mL methyl 1-methylpyrrolidine-2-carboxylate 10c (4.7 g, 33 mmol) in methylene chloride. The reaction solution under ice bath is reacted for 6 hours, 10 mL of methanol. The reaction solution was concentrated under reduced pressure, to give the title product (1-methyl - pyrrolidin-2-yl) - methanol 10d (1.8 g, brown liquid), Yield: 47.4percent.

Reference： [1] Patent: US2012/165352, 2012, A1, . Location in patent: Page/Page column 30-31
[2] Patent: TWI524893, 2016, B, . Location in patent: Page/Page column 56; 57

4
[ 638-53-9 ]
[ 498-63-5 ]
[ 3554-65-2 ]

Reference： [1] Patent: US5059628, 1991, A,
[2] Patent: EP309624, 1989, A1,

5
[ 498-63-5 ]
[ 74-88-4 ]
[ 3554-65-2 ]

Reference： [1] Patent: US5059628, 1991, A,
[2] Patent: EP309624, 1989, A1,

6
[ 74761-41-4 ]
[ 3554-65-2 ]

Reference： [1] Patent: US5001133, 1991, A,

7
[ 170491-63-1 ]
[ 3554-65-2 ]

Reference： [1] Patent: US4902684, 1990, A,

8
[ 30727-23-2 ]
[ 3554-65-2 ]

Reference： [1] Journal of the American Chemical Society, 1939, vol. 61, p. 1195,1196
[2] Collection of Czechoslovak Chemical Communications, 1958, vol. 23, p. 1413

9
[ 43041-12-9 ]
[ 3554-65-2 ]

Reference： [1] Patent: US2012/165352, 2012, A1,
[2] Patent: TWI524893, 2016, B,

10
[ 609-36-9 ]
[ 3554-65-2 ]

Reference： [1] Patent: US2012/165352, 2012, A1,
[2] Patent: TWI524893, 2016, B,

[ 3554-65-2 ] Synthesis Path-Downstream 1~88

1
5-hydroxymethyl-1,1-dimethyl-2,3-dihydro-pyrrolium; bromide [ No CAS ]
[ 3554-65-2 ]

Reference： [1]Chemicke Listy,1953,vol. 47,p. 392,397
Chem.Abstr.,1955,p. 288

2
2-Phenyl-2-<2-chlor-phenyl>-acetylchlorid [ No CAS ]
[ 3554-65-2 ]
[ 102156-75-2 ]

Reference： [1]Journal of the Chemical Society,1958,p. 4458,4462

3
[ 98-88-4 ]
[ 3554-65-2 ]
[ 61609-42-5 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1195,1196

4
[ 75-36-5 ]
[ 3554-65-2 ]
[ 61609-41-4 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1195,1196

5
[ 3554-65-2 ]
[ 74-88-4 ]
[ 118835-14-6 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1195,1196

6
[ 3554-65-2 ]
[ 58055-93-9 ]

Reference： [1]Journal of the American Chemical Society,1955,vol. 77,p. 29

7
[ 30727-23-2 ]
[ 3554-65-2 ]

Reference： [1]Journal of the American Chemical Society,1939,vol. 61,p. 1195,1196
[2]Collection of Czechoslovak Chemical Communications,1958,vol. 23,p. 1413

8
[ 18956-87-1 ]
[ 3554-65-2 ]
phenothiazine-10-carboxylic acid 1-methyl-pyrrolidin-2-ylmethyl ester [ No CAS ]

Reference： [1]Acta Chemica Scandinavica (1947),1966,vol. 20,p. 2370 - 2376

9
[ 2942-59-8 ]
[ 3554-65-2 ]
Sodium; 2-(1-methyl-pyrrolidin-2-ylmethoxy)-benzoate [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1991,vol. 34,p. 1314 - 1328

10
[ 20445-33-4 ]
[ 3554-65-2 ]
(S)-3,3,3-Trifluoro-2-methoxy-2-phenyl-propionic acid (R)-1-methyl-pyrrolidin-2-ylmethyl ester [ No CAS ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 6077 - 6088

11
[ 475-11-6 ]
[ 3554-65-2 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 6077 - 6088

12
[ 3554-65-2 ]
[ 67824-41-3 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 756 - 772

13
[ 3554-65-2 ]
4,5-difluoro-2-oxindole [ No CAS ]
7-(3,4-dimethoxy-benzyloxy)-3H-quinazoline-4-thione [ No CAS ]
4,5-difluoro-3-[7-(1-methyl-pyrrolidin-2-ylmethoxy)-quinazolin-4-yl]-1,3-dihydro-indol-2-one [ No CAS ]

Reference： [1]Tetrahedron Letters,1999,vol. 40,p. 3881 - 3884

14
[ 3554-65-2 ]
3-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-2-(4-triisopropylsilanyloxy-phenyl)-benzo[b]thiophen-6-ol [ No CAS ]
2-[4-(1-methyl-pyrrolidin-2-ylmethoxy)-phenyl]-3-[4-(2-piperidin-1-yl-ethoxy)-benzyl]-benzo[b]thiophen-6-ol [ No CAS ]

Reference： [1]Tetrahedron,1999,vol. 55,p. 11641 - 11652

16
(+-)-pyrrolidine-1,2-dicarboxylic acid diethyl ester [ No CAS ]
[ 3554-65-2 ]

Reference： [1]Journal of the Chemical Society,1958,p. 4458,4462

17
[ 103393-86-8 ]
[ 60-29-7 ]
LiAlH₄ [ No CAS ]
[ 3554-65-2 ]

Reference： [1]Journal of the Chemical Society,1958,p. 4458,4462

18
[ 52808-36-3 ]
[ 3554-65-2 ]
2-[2-(2-methoxyethoxy)ethoxymethyl]-1-methylpyrrolidine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2002,vol. 8,p. 1015 - 1023
[2]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1043 - 1045

19
[ 68832-13-3 ]
[ 74-88-4 ]
[ 3554-65-2 ]

Reference： [1]Journal of the American Chemical Society,2006,vol. 128,p. 5600 - 5601

20
[ 3251-56-7 ]
[ 3554-65-2 ]
[ 909783-58-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4872 - 4878

21
[ 3554-65-2 ]
[ 909783-62-6 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4872 - 4878

22
[ 3554-65-2 ]
4-cyclohexyl-N-[3-methoxy-4-(1-methyl-pyrrolidin-2-ylmethoxy)-phenyl]-benzamide [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,p. 4872 - 4878

23
[ 3554-65-2 ]
acetaldehyde O-(1-methyl-pyrrolidin-2-ylmethyl)-oxime [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5827 - 5830

24
[ 3554-65-2 ]
1-methyl-pyrrolidine-2-carbaldehyde O-isopropyl-oxime [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5827 - 5830

25
[ 3554-65-2 ]
1-methyl-pyrrolidine-2-carbaldehyde O-isopropyl-oxime [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5827 - 5830

26
[ 3554-65-2 ]
propan-2-one O-(1-methyl-pyrrolidin-2-ylmethyl)-oxime [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5827 - 5830

27
[ 3554-65-2 ]
propan-2-one O-(1-methyl-piperidin-3-yl)-oxime [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5827 - 5830

28
[ 3554-65-2 ]
(R)-(1-methyl-2-pyrrolidinyl)methoxylamine dihydrochloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2004,vol. 14,p. 5827 - 5830

29
N-Methyl-2-(tributylstannyl)pyrrolidine [ No CAS ]
[ 3554-65-2 ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 5763 - 5769

30
[ 3554-65-2 ]
(R)-2-Dimethylcarbamoyloxymethyl-1,1-dimethyl-pyrrolidinium; iodide [ No CAS ]

Reference： [1]Archiv der Pharmazie,1996,vol. 329,p. 95 - 104

31
[ 344-25-2 ]
[ 3554-65-2 ]

Reference： [1]Archiv der Pharmazie,1996,vol. 329,p. 95 - 104

32
[ 265660-44-4 ]
[ 3554-65-2 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 6077 - 6088

33
[ 3554-65-2 ]
[ 128510-20-3 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 756 - 772

34
[ 3554-65-2 ]
[ 128573-84-2 ]

Reference： [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 756 - 772

35
2-bromo-2-bromomethyl-1,1-dimethyl-pyrrolidinium; bromide [ No CAS ]
[ 3554-65-2 ]

Reference： [1]Chemicke Listy,1953,vol. 47,p. 392,397
Chem.Abstr.,1955,p. 288

36
1,1-dimethyl-2-methylene-pyrrolidinium; bromide [ No CAS ]
[ 3554-65-2 ]

Reference： [1]Chemicke Listy,1953,vol. 47,p. 392,397
Chem.Abstr.,1955,p. 288

37
[ 3554-65-2 ]
10-(1-methyl-pyrrolidin-2-ylmethyl)-10H-phenothiazine [ No CAS ]

Reference： [1]Acta Chemica Scandinavica (1947),1966,vol. 20,p. 2370 - 2376

38
[ 33252-30-1 ]
[ 3554-65-2 ]
[ 453560-62-8 ]

Yield	Reaction Conditions	Operation in experiment
		2-(1-Methyl-pyrrolidin-2-ylmethoxy)-4-pyridylcarbonitrile was prepared from 2-chloro-4-cyanopyridine and 1-methyl-pyrrolidin-2-ylmethanol by a procedure similar to that described in the preparation of 2-(1-methylpiperidin-4-yloxy)-4-pyridylcarbonitrile. ESI MS: (M+H)=218.

Reference： [1]Patent: US2003/225106,2003,A1 .Location in patent: Page 72

39
[ 92931-33-4 ]
[ 3554-65-2 ]
[ 895160-33-5 ]

Yield	Reaction Conditions	Operation in experiment
	In acetonitrile; at 20℃; for 3h;	To a solution of 2-bromo-N-isoxazol-3-yl-acetamide (Intermediate A) (3.9 g, 191 mmol) in acetonitrile (95 ml) is added ({R)-l-methyl-pyrrolidin-2-yl)-methanol (2.2 g, 191 mmol) in acetonitrile (5 ml). The reaction mixture is stirred at room temperature for 3 hours and then the solvent is removed in vacuo. The resulting oil is taken up in acetonitrile and ethyl acetate is then added. The resulting cloudy solution is stirred at room temperature for 30 minutes. There after, the supernatant is decanted off and the solid is dried under vacuum over two days to afford the titled compound.

Reference： [1]Patent: WO2006/66929,2006,A1 .Location in patent: Page/Page column 39

40
[ 895160-34-6 ]
[ 3554-65-2 ]

Yield	Reaction Conditions	Operation in experiment
		A cooled (00C), stirred solution of lithium aluminium hydride (200 ml of a 1 M solution in THF, 207 mmol) is treated via canula, dropwise with (R)-pyrrolidine-l,2-dicarboxylic acid 2- tert-butyl ester 1-ethyl ester (22.86 g, 94.1 mmol) in THF (300 ml). After addition, the reaction mixture is left to warm to room temperature whilst stirring over night. The solution is then treated with Rochelles salt (10 g) to partially quench the reaction and after 30 minutes, the reaction mixture is cooled (00C) and water (50 ml) is added dropwise, ensuring that the temperature does not exceed 100C. The solvent is removed in vacuo and the residue is taken up in chloroform: isopropyl alcohol (300 ml of a 7:3 mixture) and left to stir at room temperature for 3 hours. The resulting suspension is removed by filtration and the filtrate is EPO <DP n="40"/>concentrated in vacuo. The resulting oil is purified by distillation on Kugelrohr to yield the titled compound as a clear oil.

Reference： [1]Patent: WO2006/66929,2006,A1 .Location in patent: Page/Page column 38-39

41
[ 52415-29-9 ]
[ 3554-65-2 ]
[ 281204-82-8 ]

Yield	Reaction Conditions	Operation in experiment
		(b) (R)-6-Bromo-1-((N-methylpyrrolidin-2-yl)methyl)-1H-indole (208 mg, 35%); from 6-bromo-1H-indole (398.1 mg, 2.03 mmol) and <strong>[3554-65-2](R)-N-methylpyrrolidine-2-methanol</strong> (via the methanesulfonate, 467.8 mg, 4.06 mmol).

Reference： [1]Patent: US6380242,2002,B1

42
[ 35991-75-4 ]
[ 3554-65-2 ]
5-Bromo-3-((1-methyl-2-(R)-pyrrolidinyl)methoxy)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; mineral oil;	56a. 5-bromo-3-((1-methyl-2-(R)-pyrrolidinyl)methoxy)pyridine <strong>[3554-65-2](R)-1-methyl-2-pyrrolidinemethanol</strong> (430 mg, 13.74 mmol, Aldrich Chemical Co.) was dissolved in 14 mL of DMF and stirred under N2, then 123.4 mg of NaH (80% dispersion in mineral oil) was added. The reaction mixture was stirred fifteen minutes, and 897.4 mg of 3,5-dibromomethylpyridine was added. The reaction mixture was stirred at 50 C. for 16 hours. The volatiles were removed under vacuum, and the residue was purified by chromatography on silica gel to give 484 mg of the title product. MS (DCI/NH3) m/e: 271/273 (M+H)+. 1 H NMR (CDCl3, 300 MHz) delta: 8.37 (d, J=1.8, Hz, 1H), 8.26 (d, J=2.7 Hz, 1H), 7.39 (dd, J=1.8, 2.7 Hz, 11H), 4.01 (dd, J=3.3, 11.0 Hz, 1H), 3.93 (dd, J=6.9, 11.1, Hz, 1H), 3.20-3.10 (m, 11H), 3.93 (dd, J=6.9, 11.1 Hz, 1H), 3.20-3.10 (m, 1H), 2.76-2.64 (m, 1H), 2.49 (s, 3H), 2.40-2.28 (m, 1H), 2.44-2.00 (m, 4H).
	In N,N-dimethyl-formamide; mineral oil;	56a. 5-bromo-3-((1-methyl-2-(R)-pyrrolidinyl)methoxy)pyridine <strong>[3554-65-2](R)-1-methyl-2-pyrrolidinemethanol</strong> (430 mg, 13.74 mmol, Aldrich Chemical Co.) was dissolved in 14 mL of DMF and stirred under N2, then 123.4 mg of NaH (80% dispersion in mineral oil) was added. The reaction mixture was stirred fifteen minutes, and 897.4 mg of 3,5-dibromomethylpyridine was added. The reaction mixture was stirred at 50 C. for 16 hours. The volatiles were removed under vacuum, and the residue was purified by chromatography on silica gel to give 484 mg of the title product MS (DCI/NH3) m/e: 271/273 (M+H)+. 1 H NMR (CDCl3, 300 MHz) delta: 8.37 (d, J=1.8, Hz, 1H), 8.26 (d, J=2.7 Hz), 1H, 7.39 (dd, J=1.8, 2.7 Hz, 1H), 4.01 (dd, J=3.3, 11.0 Hz, 1H), 3.93 (dd, J=6.9, 11.1, Hz, 1H), 3.20-3.10 (m, 1H), 3.93 (dd, J=6.9, 11.1 Hz, 1H), 3.20-3.10 (m, 1H), 2.76-2.64 (m, 1H), 2.49 (s, 3H), 2.40-2.28 (m, 1H), 2.44-2.00 (m, 4H).
	In N,N-dimethyl-formamide; mineral oil;	5-bromo-3-((1-methyl-2-(R)-pyrrolidinyl)methoxy)pyridine <strong>[3554-65-2](R)-1-methyl-2-pyrrolidinemethanol</strong> (430 mg, 13.74 mmol) was dissolved in 14 mL of DMF and stirred under N2, then 123.4 mg of NaH (80% dispersion in mineral oil) was added. The reaction mixture was stirred fifteen minutes, and 897.4 mg of 3,5-dibromomethylpyridine was added. The reaction mixture was stirred at 50 C. for 16 hours. The volatiles were removed under vacuum, and the residue was purified by chromatography on silica gel to give 484 mg of the title product. MS (CI/NH3) m/z 271/273 (M+H)+. 1 H NMR (CDCl3, 300 MHz) delta: 8.37 (d, J=1.8, Hz, 1H), 8.26 (d, J=2.7 Hz, 1H), 7.39 (dd, J=1.8, 2.7 Hz, 1H), 4.01 (dd, J=3.3, 11.0 Hz, 1H), 3.93 (dd, J=6.9, 11.1, Hz, 1H), 3.20-3.10 (m, 1H), 3.93 (dd, J=6.9, 11.1 Hz, 1H), 3.20-3.10 (m, 1H), 2.76-2.64 (m, 1H), 2.49 (s, 3H), 2.40-2.28 (m, 1H), 2.44-2.00 (m, 4H).

	In N,N-dimethyl-formamide; mineral oil;	5-bromo-3-((1-methyl-2-(R)-pyrrolidinyl)methoxy)pyridine <strong>[3554-65-2](R)-1-methyl-2-pyrrolidinemethanol</strong> (430 mg, 13.74 mmol) was dissolved in 14 mL of DMF and stirred under N2, then 123.4 mg of NaH (80% dispersion in mineral oil) was added. The reaction mixture was stirred fifteen minutes, and 897.4 mg of 3,5-dibromomethylpyridine was added. The reaction mixture was stirred at 50 C. for 16 hours. The volatiles were removed under vacuum, and the residue was purified by chromatography on silica gel to give 484 mg of the title product. MS (DCI/NH3) m/z 271/273 (M+H)+. 1 H NMR (CDCl3, 300 MHz) delta: 8.37 (d, J=1.8, Hz, 1H), 8.26 (d, J=2.7 Hz, 1H), 7.39 (dd, J=1.8, 2.7 Hz, 1H), 4.01 (dd, J=3.3, 11.0 Hz, 1H), 3.93 (dd, J=6.9, 11.1, Hz, 1H), 3.20-3.10 (m, 1H), 3.93 (dd, J=6.9, 11.1 Hz, 1H), 3.20-3.10 (m, 1H), 2.76-2.64 (m, 1H), 2.49 (s, 3H), 2.40-2.28 (m, 1H), 2.44-2.00 (m, 4H).
	In N,N-dimethyl-formamide; mineral oil;	5-Bromo-3-((1-methyl-2-(R)-pyrrolidinyl)methoxy)pyridine <strong>[3554-65-2](R)-1-methyl-2-pyrrolidinemethanol</strong> (430 mg, 13.74 mmol) was dissolved in 14 mL of DMF and stirred under N2, then 123.4 mg of NaH (80% dispersion in mineral oil) was added. The reaction mixture was stirred fifteen minutes, and 897.4 mg of 3,5-dibromomethylpyridine was added. The reaction mixture was stirred at 50 C. for 16 hours. The volatiles were removed under vacuum, and the residue was purified by chromatography on silica gel to give 484 mg of the title product. MS (CI/NH3) m/z 271/273 (M+H)+. 1H NMR (CDCl3, 300 MHz) delta: 8.37 (d, J=1.8, Hz, 1H), 8.26 (d, J=2.7 Hz, 1H), 7.39 (dd, J=1.8, 2.7 Hz, 1H), 4.01 (dd, J=3.3, 11.0 Hz, 1H), 3.93 (dd, J=6.9, 11.1 Hz, 1H), 3.20-3.10 (m, 1H), 3.93 (dd, J=6.9, 11.1 Hz, 1H), 3.20-3.10 (m, 1H), 2.76-2.64 (m, 1H), 2.49 (s, 3H), 2.40-2.28 (m, 1H), 2.44-2.00 (m, 4H).

Reference： [1]Patent: US5914328,1999,A
[2]Patent: US5948793,1999,A
[3]Patent: US6127386,2000,A
[4]Patent: US5629325,1997,A
[5]Patent: US6437138,2002,B1

43
[ 141-30-0 ]
[ 3554-65-2 ]
2-((1-methyl-2-(R)-pyrrolidinyl)methoxy)-6-chloropyridazine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
42%	With NaH; In tetrahydrofuran; mineral oil;	5a. 2-((1-methyl-2-(R)-pyrrolidinyl)methoxy)-6-chloropyridazine (R)-1-Methyl-2-pyrrolidinemethanol (300 mg, 2.61 mmol) was dissolved in anhydrous THF and cooled to 0 C. with stirring. NaH (80% dispersion in mineral oil, 0.082 g, 2.9 mmol) was added and the mixture was slowly warmed to room temperature with stirring. After 30 minutes a THF solution of 3,6-dichloropyridazine (0.41 g, 2.74 mmol) was added to the mixture via syringe. The reaction was stirred for 48 hours. The solvent was then evaporated in vacuo and the mixture diluted with chloroform, washed with saturated NaHCO3 and then with brine. The organic layer was dried over MgSO4. The resulting crude material was purified by flash chromatography (10% MeOH/CHCl3) to give 0.25 g (42% yield) of the title compound as a cream colored solid. MS (DCI/NH3) m/e 228 (M+H)+. [alpha]25D =+32 (c=1, MeOH).

Reference： [1]Patent: US5948793,1999,A

44
[ 85148-26-1 ]
[ 3554-65-2 ]
3-((1-methyl-2-(R)-pyrrolidinyl)methoxy)-5-trifluoromethylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In N,N-dimethyl-formamide; mineral oil;	54a. 3-((1-methyl-2-(R)-pyrrolidinyl)methoxy)-5-trifluoromethylpyridine <strong>[3554-65-2](R)-1-methyl-2-pyrrolidinemethanol</strong> (Aldrich Chemical Co.) was dissolved in 8 mL of DMF and stirred under N2, then 240 mg of NaH (80% dispersion in mineral oil) was added. The reaction mixture was stirred fifteen minutes, and 363 mg of 3-chloro-5-trifluoromethylpyridine (2.0 mmol) was added. The reaction mixture was stirred at 50 C. for 16 hours. The volatiles were removed under vacuum, and the residue was purified by chromatography on silica gel, eluding with 2:1 ethyl acetate:hexane to give 336 mg of the title product. MS (DCI/NH3) m/e: 261 (M+H)+. 1 H NMR (CDCl3, 300 MHz) delta: 8.50 (d, J=0.6 Hz, 1H), 8.49 (d, J=3.0 Hz, 1H), 7.41 (dd, J=0.6, 3.0 Hz, 1H), 4.12-3.96 (m, 2H), 3.21-3.10 (m, 1H), 2.80-2.65 (m, 1H), 2.51 (s, 3H), 2.44-2.30 (m, 1H), 2.13-1.73 (m, 4H).

Reference： [1]Patent: US5914328,1999,A

45
[ 74761-41-4 ]
[ 3554-65-2 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; tetrahydrofuran.A; water;	(b) (-)-2-hydroxymethyl-N-methyl-pyrrolidine 46 g lithium aluminium hydride are suspended in 500 ml tetrahydrofuran.A solution of 52 g N-methoxycarbonyl-L-proline in 500 ml tetrahydrofuran is added to the resultant suspension at 20° to 35° C. The mixture is heated to reflux temperature and refluxed for 24 hours. The mixture is then cooled to -10° and carefully treated dropwise with a mixture of 125 ml water and 125 ml tetrahydrofuran at -10 to 0°. The mixture is allowed to react at room temperature and forms a white suspension. The white suspension is filtered off and the filter residue extracted three times with methylene chloride. The extracts are combined with the filtrate. The mixture is concentrated under a vacuum at 50° to give 32 g of an oil. This oil is distilled (17 mm Hg) under water vacuum.

Reference： [1]Patent: US5001133,1991,A

46
[ 80-48-8 ]
[ 3554-65-2 ]
1,1-dimethyl-2-hydroxymethylpyrrolidinium p-toluenesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone;	REFERENCE EXAMPLE 3 1,1-Dimethyl-2-hydroxymethylpyrrolidinium p-toluenesulfonate In 10 ml of acetone was dissolved 1.47 g of 1-methyl-2-pyrrolidinemethanol, and 2.38 g of methyl p-toluenesulfonate was added dropwise to the resulting solution. The mixture was stirred at room temperature, heated under reflux, and cooled to precipitate crystals. The crystals were collected by filtration and dried to give 2.67 g of the desired compound. 1 H NMR (DMSO-d6) delta: 1.5-2.2 (m, 4H), 2.28 (s, 3H), 2.94 (s, 3H), 3.17 (s, 3H), 3.3-3.9 (m, 5H), 5.25-5.5 (m, 1H), 6.95-7.6 (m, 4H). IR (KBr) cm-1: 3400, 3050, 2960, 2900, 1475, 1190, 1130, 1040, 1015, 820, 690, 575.

Reference： [1]Patent: US4962096,1990,A

47
[ 3554-65-2 ]
[ 54288-69-6 ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform;	(C) R-2-(Chloromethyl)-1-methylpyrrolidine, hydrochloride To a solution of R-N-methyl-2-pyrrolidinemethanol (2.O g, 17.4 mmol) in chloroform (18 ml) at 0° C. was added dropwise thionyl chlrride (0.74 g, 52.1 mmol). The reaction mixture was heated to reflux for 2 hours, and then cooled to room temperature and concentrated at reduced pressure. The residue was recrystallized from acetone-ether to yield the title compound as a pale yellow solid (1.14 g).

Reference： [1]Patent: US4902684,1990,A

48
aqueous sodium sulfate [ No CAS ]
[ 170491-63-1 ]
[ 3554-65-2 ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran;	(B) R-N-Methyl-2-pyrrolidinemethanol Lithium aluminum hydride (7.6 g, 200 mmol) was added in small portions to dry tetrahydrofuran (200 ml) cooled to 0°-5° C. A solution of R-N-(t-butoxycarbonyl)-2-pyrrolidinemethanol (13 g crude, 50 mmol) in dry tetrahydrofuran (100 ml) was then added dropwise with vigorous stirring over a period of 45 minutes. After 30 minutes at 0° C. room temperature, the reaction mixture was heated to reflux for 16 hours. The reaction mixture was then cooled to 0° C. and the excess hydride was destroyed by a slow addition of saturated aqueous sodium sulfate. Addition was continued until all the inorganic salts were precipitated as a white granular solid. The mixture was diluted with ethyl acetate (500 ml), dried lmagnesium sulfate), filtered and concentrated to give the title compound as a colorless oil (5.7 g). The crude product was used without purification in the next reaction

Reference： [1]Patent: US4902684,1990,A

49
[ 498-63-5 ]
[ 74-88-4 ]
[ 3554-65-2 ]

Yield	Reaction Conditions	Operation in experiment
	With n-butyllithium; In tetrahydrofuran; water;	REFERENCE EXAMPLE 22 Five grams (0.050 mol) of prolinol were treated with double the equivalent of n-butyl lithium in tetrahydrofuran at -70° C., and 7.0 g of methyl iodide was added dropwise thereto at -70° C., followed by stirring for 2 hours. The temperature was gradually elevated, and the reaction was further continued for an additional hours under ice-cooling. To the reaction mixture was added 1.8 g of water, and the precipitate thus formed was removed by filtration. The filtrate was concentrated, and the concentrate was purified by column chromatography to obtain 3.0 g of N-methylprolinol.
	With n-butyllithium; In tetrahydrofuran; water;	REFERENCE EXAMPLE 22 Five grams (0.050 mol) of prolinol were treated with double the equivalent of n-butyl lithium in tetrahydrofuran at -70°C, and 7.0 g of methyl iodide was added dropwise thereto at -70°C, followed by stirring for 2 hours. The temperature was gradually elevated, and the reaction was further continued for an additional 2 hours under ice-cooling. To the reaction mixture was added 1.8 g of water, and the precipitate thus formed was removed by filtration. The filtrate was concentrated, and the concentrate was purified by column chromatography to obtain 3.0 g of N-methylprolinol.

Reference： [1]Patent: US5059628,1991,A
[2]Patent: EP309624,1989,A1

50
[ 75-44-5 ]
[ 3554-65-2 ]
[ 119833-59-9 ]

Yield	Reaction Conditions	Operation in experiment
1.8 g (25%)	With hydrogenchloride; sodium hydroxide; In dichloromethane; triethylamine;	PREPARATION 23 4-[(3-Chloro)propyl]-3-methyl-2-oxazolidinone A cold (ice bath) solution of 4.0 g (0.041 mole) of phosgene dissolved in 50 ml of methylene chloride was treated dropwise with a solution of 4.7 g (0.041 mole) of 2-hydroxymethyl-1-methylpyrrolidine in 15 ml of methylene chloride at such a rate that the temperature did not exceed 10° C. After addition was complete, the solution was stirred in the cold for 1 hr and then treated dropwise with 4.0 g (0.041 mole) of triethylamine at such a rate that the temperature did not exceed 25° C. The mixture was stirred at ambient temperature for 3 hr and then treated with 50 ml of 1N hydrochloric acid. The layers were separated and the organic layer was washed successively with 50 ml of 1N hydrochloric acid, 50 ml of 4percent sodium hydroxide, and 50 ml of brine. The organic layer was dried over sodium sulfate and concentrated to give 2.5 g of oil as residue. This oil was purified by column chromatography on 50 g of silica gel eluted with benzene. Fractions containing the desired product were combined and concentrated to give 1.8 g (25percent) of product as an oil.

Reference： [1]Patent: US4886794,1989,A

51
[ 502767-50-2 ]
[ 3554-65-2 ]
[ 676360-92-2 ]

Yield	Reaction Conditions	Operation in experiment
20%		Example 114 Synthesis of N2-(3-chloro-4-methoxyphenyl)-N4-cycloheptyl-6-(1-methyl-2-azolanylmethoxy)-1,3,5-triazine-2,4-diamine (E25) A mixture of N-methyl prolinol (0.226 g, 1.96 mmol) and sodium hydroxide (79 mg, 1.96 mmol) in benzene (10 mL) was heated to reflux for 2 hours with stirring under nitrogen atmosphere and then cooled to 25° C. followed by the addition of compound 133 (0.25 g, 0.65 mmol) at same temperature. The mixture was heated to reflux for 6 hours, concentrated under vacuum and diluted with water (3 mL). The gum which separated was collected (by decanting out the liquid portion) and purified by column chromatography (1-3percent MeOH-CHCl3) to afford the title compound E25 as a semi-solid (0.06 g, 20percent). HPLC: Symmetry shield RP18 (250*4.6 mm) 5 microns [solvent A=0.01 M KH2PO4 (pH 3.0); solvent B=CH3CN], Gradient elution program: T/percent B=0/35, 10/35, 40/80, 50/80, 55/35, 60/35; 270 nm, Rt 15.51 min, 99.55percent purity; MS (CI): m/z 461 (M+H, 100).
20%		A mixture of N-methyl prolinol (0.226 g, 1.96 mmol) and sodium hydroxide (79 mg, 1.96 mmol) in benzene (10 mL) was heated to reflux for 2 hours with stirring under nitrogen atmosphere and then cooled to 25° C. followed by the addition of compound 133 (0.25 g, 0.65 mmol) at same temperature. The mixture was heated to reflux for 6 hours, concentrated under vacuum and diluted with water (3 mL). The gum which separated was collected (by decanting out the liquid portion) and purified by column chromatography (1-3percent MeOH-CHCl3) to afford the title compound E25 as a semi-solid (0.06 g, 20percent). HPLC: Symmetry shield RP18 (250*4.6 mm) 5 microns [solvent A=0.01 M KH2PO4 (pH 3.0); solvent B=CH3CN], Gradient elution program: T/percent B=0/35, 10/35, 40/80, 50/80, 55/35, 60/35; 270 nm, Rt 15.51 min, 99.55percent purity; MS (CI): m/z 461 (M+H, 100).
20%		A mixture of N-methyl prolinol (0.226 g, 1.96 mmol) and sodium hydroxide (79 mg, 1.96 mmol) in benzene (10 mL) was heated to reflux for 2 hours with stirring under nitrogen atmosphere and then cooled to 25° C. followed by the addition of compound 133 (0.25 g, 0.65 mmol) at same temperature. The mixture was heated to reflux for 6 hours, concentrated under vacuum and diluted with water (3 mL). The gum which separated was collected (by decanting out the liquid portion) and purified by column chromatography (1-3percent MeOH-CHCl3) to afford the title compound E25 as a semi-solid (0.06 g, 20percent). HPLC: Symmetry shield RP18 (250*4.6 mm) 5 microns [solvent A=0.01 M KH2PO4 (pH 3.0); solvent B=CH3CN], Gradient elution program: T/percent B=0/35, 10/35, 40/80, 50/80, 55/35, 60/35; 270 nm, Rt 15.51 min, 99.55percent purity; MS (CI): m/z 461 (M+H, 100).

20%		A mixture of N-methyl prolinol (0.226 g, 1.96 mmol) and sodium hydroxide (79 mg, 1.96 mmol) in benzene (10 mL) was heated to reflux for 2 hours with stirring under nitrogen atmosphere and then cooled to 25 C followed by the addition of compound133 (0.25 g, 0.65 mmol) at same temperature. The mixture was heated to reflux for 6 hours, concentrated under vacuum and diluted with water (3 mL). The gum which separated was collected (by decanting out the liquid portion) and purified by column chromatography (1-3 percentMeOH-CHCI3) to afford the title compoundE25 as a semi-solid (0.06 g, 20percent). HPLC: Symmetry shieldRP18 (250 x 4.6 mm)5 microns [solvent A = 0.01 MKH2P04 (pH 3.0) ; solvent B =CH3CN], Gradient elution program:T/percent B= 0/35, 10/35,40/80,50/80,55/35, 60/35; 270 nm, Rt 15.51 min, 99.55 percent purity ; MS(CI) : m/z 461 (M+H, 100).
	With sodium hydroxide; In benzene;	Example 114 Synthesis of N2-(3-chloro-4-methoxyphenyl)-N4-cycloheptyl-6-(1-methyl-2-azolanylmethoxy)-1,3,5-triazine-2,4-diamine (E25) A mixture of N-methyl prolinol (0.226 g, 1.96 mmol) and sodium hydroxide (79 mg, 1.96 mmol) in benzene (10 mL) was heated to reflux for 2 hours with stirring under nitrogen atmosphere and then cooled to 25° C. followed by the addition of compound 133 (0.25 g, 0.65 mmol) at same temperature. The mixture was heated to reflux for 6 hours, concentrated under vacuum and diluted with water (3 mL). The gum which separated was collected (by decanting out the liquid portion) and purified by column chromatography (1-3percent MeOH-CHCl3) to afford the title compound E25 as a semi-solid (0.06 g, 20percent). HPLC: Symmetry shield RP18 (250*4.6 mm) 5 microns [solvent A=0.01 M KH2PO4 (pH 3.0); solvent B=CH3CN], Gradient elution program: T/percentB=0/35, 10/35, 40/80, 50/80, 55/35, 60/35; 270 nm, Rt 15.51 min, 99.55percent purity; MS (CI): m/z 461 (M+H, 100).

Reference： [1]Patent: US2004/209880,2004,A1 .Location in patent: Page/Page column 110
[2]Patent: US2004/209881,2004,A1 .Location in patent: Page/Page column 128
[3]Patent: US2004/209882,2004,A1 .Location in patent: Page/Page column 125-126
[4]Patent: WO2004/26844,2004,A1 .Location in patent: Page 382
[5]Patent: US2004/224950,2004,A1

52
[ 45223-18-5 ]
[ 3554-65-2 ]
2Br^(1-)*C₂₈H₅₈N₂O₂⁽²⁺⁾ [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 6307 - 6315

53
[ 1260006-62-9 ]
[ 3554-65-2 ]
[ 1260010-10-3 ]

Yield	Reaction Conditions	Operation in experiment
5%	With 18-crown-6 ether; potassium carbonate; potassium hydroxide; In toluene; at 20℃; for 24h;Reflux;	Example 181Preparation of 1-Benzothiazol-6-yl-3-[4-(1-methyl-pyrrolidin-2-ylmethoxy)-pyridin-3-yl]-imidazolidin-2-one (181A) 1-Benzothiazol-6-yl-3-(4-chloro-pyridin-3-yl)-imidazolidin-2-one (I-180a: 100 mg, 0.3023 mmol) was added to a stirred mixture of KOH (68 mg, 1.2092 mmol), K2CO3 (42 mg, 0.3023 mmol) and toluene (3 mL) and the reaction mixture was stirred at RT for 5 mins. This was followed by the addition of (1-methyl-pyrrolidin-2-yl)-methanol (52 mg, 0.4534 mmol) and 18 crown ether (8 mg, 0.0302 mmol) and the resulting mixture was refluxed for 24 hrs. The reaction was monitored by TLC (10percent MeOH in CHCl3). The reaction mixture was concentrated and the concentrate was partitioned between ethylacetate and water. The organic layer was washed with water, brine, dried over Na2SO4 and concentrated. Purification by preparative HPLC afforded 6 mg of the product (5percent yield).1H NMR (300 MHz, CDCl3): delta 8.9 (s, 1H), 8.55 (s, 1H), 8.45 (d, 1H), 8.35 (d, 1H), 8.1 (d, 1H) 7.7 (dd, 1H), 6.9 (d, 1H), 4.2-3.9 (m, 7H), 3.1 (t, 1H), 2.7 (bs, 1H), 2.45 (s, 3H), 2.35-2.2 (m, 1H), 2.05-1.95 (m, 1H), 1.85-1.7 (m, 2H).LCMS: 100percent, m/z=410 (M+1)HPLC: 96.12percent
5%		1 -Bon/othia/ol-6-yl-3-(,4-chloro-pyridin-3-yl)-imida/olidin-2-otauie (1-18Oa: lOOmg, 0.3023miotanol) wa.s added to a stirred mixture of KOH (68mg, 1.2092mmoelkappa R;C'f>i (42mg. O.3023mmol) and toluene (3iotanL) and the reaction mixture was Mirrod at U V for 5mins. This was followed b> the addition of (l -mcthyl-pyrrolidin-2-yl)-iotanethanol (52mg, 0.4534mmol) and 18 crown ether <8mg, O.0302mmol) and the resulting mixture was re fluxed for 24hrs. The reaction was monitored bs I LC H0percent McOI I in CHCh). 1 he ieaction mixture was concentrated and the concentrate was partitioned between cthy lacetate and water. T he organic layer was washed with water, brine, dried over Na;SO.t and concentrated. Purification by preparative I IPLC afforded 6mg of the product (5percent yield). . H NMR <300 MH/. CDCH): Lambda 8.9 (s. 111), 8.55 (s. 111), 8.45 (d. 111). 8.35 (d.I H). 8.1 (d. 111 ) 7.7 (dd. I H). 6.9 (d. 111). 4.2-3 9 (m. 710, 3.1 (U I I I). 2.7 (bs. I H). 2.45 (s. 3H), 2.35-2.2 (in, I H). 2.05-1 .95 (m, I H). 1.85-1.7 (m. 2\\ \\ LCMS: 100percent. m// - 410 {M U> HPLC: 96.12percent

Reference： [1]Patent: US2010/331326,2010,A1 .Location in patent: Page/Page column 75
[2]Patent: WO2010/149755,2010,A1 .Location in patent: Page/Page column 191-192

54
[ 864757-74-4 ]
[ 3554-65-2 ]
4-(benzyloxy)-1-(4-[(1-methylpyrrolidin-2-yl)methoxy]-phenyl)pyridin-2(1H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%	With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 20℃; for 4h;	General procedure: To a solution of 4-(4-fluorophenyl)-1-(4-hydroxyphenyl)pyridin-2(1H)-one (12, 40 mg, 0.142 mmol), PPh3 (56 mg, 0.213 mmol), 2-(piperidin-1-yl)ethanol (0.025 mL, 0.170 mmol) in THF (2 mL) was added diethyl azodicarboxylate (37 mg, 0.213 mmol). The mixture was stirred at room temperature for 4 h and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (MeOH/CHCl3) and crystallized (EtOAc/hexane) to give compound 5a (41 mg, 73percent) as a white solid.

Reference： [1]Bioorganic and Medicinal Chemistry,2011,vol. 19,p. 883 - 893

55
[ 42523-29-5 ]
[ 3554-65-2 ]
2,7-bis[(2R)-1-methylpyrrolidin-2-ylmethoxy]-fluoren-9-one [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 1633 - 1638

56
[ 69610-40-8 ]
[ 3554-65-2 ]

Yield	Reaction Conditions	Operation in experiment
77%	With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h;Cooling with ice; Reflux;	Step 1 [(2R)-1-Methylpyrrolidin-2-yl]methanol Lithium aluminium hydride (230 mg, 6 mmol) and N-tert-butoxycarbonyl-L-prolinol 5a (400 mg, 2 mmol) were dissolved in 10 mL of dry tetrahydrofuran in an ice-water bath in batches. After no gas was released obviously, the reaction mixture was heated to reflux for 2 hours. The reaction mixture was added dropwise with 5 mL of methanol in an ice-water bath, followed by addition of 5 mL of water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to obtain the title compound [(2R)-1-methylpyrrolidin-2-yl]methanol 5b (221 mg, yield 77.0%) as a colourless oil. MS m/z (ESI): 116 [M+1]

Reference： [1]Patent: US2012/165352,2012,A1 .Location in patent: Page/Page column 23-24

57
[ 23356-96-9 ]
[ 3554-65-2 ]

Reference： [1]Patent: US2012/165352,2012,A1

58
[ 43041-12-9 ]
[ 3554-65-2 ]

Reference： [1]Patent: US2012/165352,2012,A1
[2]Patent: TWI524893,2016,B

59
[ 609-36-9 ]
[ 3554-65-2 ]

Reference： [1]Patent: US2012/165352,2012,A1
[2]Patent: TWI524893,2016,B

60
[ 933-94-8 ]
[ 3554-65-2 ]

Yield	Reaction Conditions	Operation in experiment
47.4%		Step 3(1-Methylpyrrolidin-2-yl)methanolDiisobutyl aluminium hydride (60 mL, 66 mmol) was added dropwise to a solution of methyl 1-methylpyrrolidine-2-carboxylate 10c (4.7 g, 33 mmol) in 50 mL of dichloromethane.The reaction mixture was stirred for 6 hours in an ice-water bath, followed by addition of 10 mL of methanol.The reaction mixture was concentrated under reduced pressure to obtain the title compound (1-methylpyrrolidin-2-yl)methanol 10d (1.8 g, yield 47.4percent) as a brown oil.
1.8 g	With diisobutylaluminium hydride; In dichloromethane; for 6h;Cooling with ice; Inert atmosphere;	Diisobutylaluminum hydride (60 mL, 66 mmol) was added dropwise to 50 mL methyl 1-methylpyrrolidine-2-carboxylate 10c (4.7 g, 33 mmol) in methylene chloride. The reaction solution under ice bath is reacted for 6 hours, 10 mL of methanol. The reaction solution was concentrated under reduced pressure, to give the title product (1-methyl - pyrrolidin-2-yl) - methanol 10d (1.8 g, brown liquid), Yield: 47.4percent.

Reference： [1]Patent: US2012/165352,2012,A1 .Location in patent: Page/Page column 30-31
[2]Patent: TWI524893,2016,B .Location in patent: Page/Page column 56; 57

61
[ 3554-65-2 ]
[ 1269662-73-8 ]

Reference： [1]Patent: US2012/165352,2012,A1
[2]Patent: EP2684877,2014,A2
[3]Patent: US2013/338190,2013,A1
[4]Patent: TWI524893,2016,B

62
[ 3554-65-2 ]
[ 1269662-76-1 ]

Reference： [1]Patent: US2012/165352,2012,A1
[2]Patent: TWI524893,2016,B

63
[ 3554-65-2 ]
[ 1269662-77-2 ]

Reference： [1]Patent: US2012/165352,2012,A1
[2]Patent: TWI524893,2016,B

64
[ 3554-65-2 ]
[ 13493-88-4 ]

Yield	Reaction Conditions	Operation in experiment
56.8%		Step 41-Methylpyrrolidine-2-carbaldehydeDimethyl sulfoxide (2.2 mL, 31.20 mmol) was dissolved in 20 mL of dichloromethane in a dry ice-acetone bath, followed by addition of oxalyl chloride (2 mL, 23.40 mmol).After stirring for 45 minutes at -18° C., (1-methylpyrrolidin-2-yl)methanol 10d (1.8 g, 15.60 mmol) was added.After stirring for another 45 minutes, triethylamine (6.5 mL, 46.80 mmol) was added.The reaction mixture was warmed up to room temperature and stirred for 1 hour.The reaction mixture was washed with saturated brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure and the resulting residue was purified by alkaline alumina column chromatography with elution system A to obtain 1-methylpyrrolidine-2-carbaldehyde 10e (1 g, yield 56.8percent) as a brown oil.
56.8%		Dimethyl sulfoxide (2.2 mL, 31.20 mmol) was dissolved in 20 mL of methylene chloride. Under dry ice-acetone bath, add oxalyl chloride (2 mL, 23.40 mmol) and allow to react at -18 deg.C for 45 min. Add ( 1-methyl - pyrrolidin-2-yl)methanol 10d (1.8 g, 15.60 mmol). After 45 minutes, add triethylamine (6.5 mL, 46.80 mmol). Naturally warm room temperature. React for one hour. The reaction mixture was washed with saturated sodium chloride solution (50 mL), dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated and purified by column chromatography on basic alumina eluting A surfactant system resulting residue was 1- methyl - pyrrolidine-2-carbaldehyde 10e (1 g, brown liquid), yield: 56.8percent.

Reference： [1]Patent: US2012/165352,2012,A1 .Location in patent: Page/Page column 30-31
[2]Patent: TWI524893,2016,B .Location in patent: Page/Page column 56; 57

65
[ 50-00-0 ]
[ 498-63-5 ]
[ 3554-65-2 ]

Yield	Reaction Conditions	Operation in experiment
56%	With hydrogen;palladium 10% on activated carbon; In water; for 18h;	a) (/?S)-(1 -Methylpyrrolidin-2-yl)methanoIA mixture of (RS)-pyrrolidin-2-ylmethanol (1.00 g, 9.90 mrnol, 1.0 eq), formaldehyde (35percent aqueous, 10 mL) and 10percent Pd/C (200 mg) was stirred under a balloon of hydrogen gas for 18 h. The mixture was filtered through a Celite pad, concentrated under reduced pressure and purification by silica gel chromatography (20percent MeOH/CHCI3) gave a colorless liquid (650 mg, 56percent); 1H NMR (400 MHz, CDCI3) 6 ppm 3.65 (dd, =10.0, 3.6 Hz, 1 H), 3.43 (dd, J=10.8, 2.0 Hz, 1H), 3.10-3.05 (m, 1 H), 2.40-2.35 (m, 1 H), 2.33 (s, 3H), 2.32-2.25 (m, 1 H), 1.93-1.68 (m, 4H); m/z (APCIf: 116 [M+H]+.

Reference： [1]Patent: WO2012/127212,2012,A1 .Location in patent: Page/Page column 101

66
[ 3554-65-2 ]
[ 19333-10-9 ]
[ 1415223-96-9 ]

Yield	Reaction Conditions	Operation in experiment
61.2%	With sodium hydride; In toluene; for 6h;Inert atmosphere; Reflux;	General procedure: A mixture of unsubstituted dichloro [phthalocyaninato] silicon (1) (50 mg, 0.0817 mmol), NaH (0.735 mmol, 17.6 mg) and (1-methylpyrrolidin-2-yl)methanol (28.21 mg, 0.245 mmol) for compound 2, 2-(azepan-1-yl)ethanol (35.08 mg, 0.245 mmol) for compound 3 or 2,4,6-tris(N,N-dimethylaminomethyl) phenol (65 mg, 0.245 mmol) for compound 4 in dry toluene (25 mL) was refluxed for 6 h under N2. After the reaction mixture was centrifuged, the filtrate was evaporated and the residue was washed with n-hexane (3 30 mL) and dried in vacuo.

Reference： [1]Inorganica Chimica Acta,2013,vol. 394,p. 353 - 362

67
[ 69411-67-2 ]
[ 3554-65-2 ]
[ 1428555-25-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride; In tetrahydrofuran; at 0 - 20℃; for 48h;	General procedure: A vial was charged with 2-trifluoromethyl, 5-nitroflurobenzaldehyde (1.4 mmol), various aminoalcohols (1.4 mmol) and anhydrous tetrahydrofuran (10 mL). The reagents were stirred vigorously and cooled to 0 C in an ice-water bath. Sodium hydride (2.8 mmol) was added portionwise to the mixture over 5 minutes and the resulting suspension warmed to room temperature and stirred for 48 hours. The reaction was quenched by the addition of water (5 mL) and brine (5 mL) and product extracted into diethyl ether. The organic layer was dried, decolorized with activated charcoal, filtered, and evaporated in vacuo to afford the crude product that was purified on silica with methanol/ethyl acetate as the eluent.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2177 - 2180

68
[ 3554-65-2 ]
[ 1428555-18-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2177 - 2180

69
[ 3554-65-2 ]
C₁₃H₁₇F₃N₂O [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2013,vol. 23,p. 2177 - 2180

70
[ 3554-65-2 ]
(R,E)-N-(4-(3-chloro-4-(pyridine-2-ylmethoxy)phenylamino)-3-cyano-7-ethoxyquinoline-6-yl)-3-(1-methylpyrrolidinyl-2-yl)acrylamide dimaleate salt [ No CAS ]

Reference： [1]Patent: EP2684877,2014,A2
[2]Patent: US2013/338190,2013,A1

71
[ 3554-65-2 ]
(E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide methanesulfonate [ No CAS ]

Reference： [1]Patent: EP2684877,2014,A2
[2]Patent: US2013/338190,2013,A1

72
[ 3554-65-2 ]
(E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide dimethanesulfonate [ No CAS ]

Reference： [1]Patent: EP2684877,2014,A2
[2]Patent: US2013/338190,2013,A1

73
[ 3554-65-2 ]
(E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide trimethanesulphonate [ No CAS ]

Reference： [1]Patent: EP2684877,2014,A2
[2]Patent: US2013/338190,2013,A1

74
[ 3554-65-2 ]
(E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide p-toluenesulfonate [ No CAS ]

Reference： [1]Patent: EP2684877,2014,A2
[2]Patent: US2013/338190,2013,A1

75
[ 3554-65-2 ]
(E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide succinate [ No CAS ]

Reference： [1]Patent: EP2684877,2014,A2
[2]Patent: US2013/338190,2013,A1

76
[ 3554-65-2 ]
(E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide dihydrochloride [ No CAS ]

Reference： [1]Patent: EP2684877,2014,A2
[2]Patent: US2013/338190,2013,A1

77
[ 59378-81-3 ]
[ 3554-65-2 ]

Yield	Reaction Conditions	Operation in experiment
77.0%	With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h;Reflux; Inert atmosphere; Cooling with ice;	Step 1 [(2R)-1-Methylpyrrolidin-2-yl]methanol Lithium aluminium hydride (230 mg, 6 mmol) and N-tert-butoxycarbonyl-R-prolinol 1a (400 mg, 2 mmol) were dissolved in 10 mL of dry tetrahydrofuran in an ice-water bath in batches. After no gas was obviously released, the reaction mixture was heated to reflux for 2 hours. The reaction mixture was added dropwise to 5 mL of methanol in an ice-water bath, followed by addition of 5 mL of water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound [(2R)-1-methylpyrrolidin-2-yl]methanol 1b (221 mg, yield 77.0%) as a colourless oil. MS m/z (ESI): 116 [M+1].
77%	With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h;Cooling with ice; Reflux;	Lithium aluminium hydride (230 mg, 6 mmol) and N-tert-butoxycarbonyl- R-prolinol la (400 mg, 2 mmol) were dissolved in 10 mL of dry tetrahydrofuran in an ice-water bath in batches. After no gas was released obviously, the reaction mixture was heated to reflux for 2 hours. The reaction mixture was added dropwise with 5 mL of methanol in an ice-water bath, followed by addition of 5 mL of water, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure to give the title compound [(2R)-1-methylpyrrolidin-2-yl]methanol 1b (221 mg, yield 77.0%) as a colourless oil. MS m/z (ESI): 116 [M+1]
77%	With lithium aluminium tetrahydride; In tetrahydrofuran; for 2h;Cooling with ice; Reflux; Inert atmosphere;	Under ice-cooling, portionwise add lithium aluminum hydride (230 mg, 6 mmol) and N-tert-butoxycarbonyl-(R)-prolinol 5a (400 mg, 2 mmol) to 10 mL of dry tetrahydrofuran solution until no gas after generation. The reaction was refluxed for 2 hours. Under ice-cooling, was slowly added dropwise 5 mL of methanol and then 5 mL of water, was added over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give the title product [(2R) -1- methyl-pyrrolidin-2-yl] methanol 5b (221 mg, colorless liquid). yield: 77%.

67.1%

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 - 65℃;

To a solution of (R)-tert-butyl 2-(hydroxymethyl)pyrrolidine- 1 -carboxylate (5.8 g, 29.0 mmol) in THF (anhydrous, 60 mL) was added lithium aluminum hydride (3.28 g, 28.8mmol) in portions at 0C, and the reaction was stirred to 65C overnight. The mixture was quenched by aqueous sodium hydroxide solution (3.28 mL, 15% wt) and water (3.28 mL+ 9.84 mL). The slurry was filtered, and the filter cake was washed with ethyl acetate twice. The combined filtrates were dried over sodium sulfate and concentrated to give (R)-(imethylpyrrolidin-2-yl)methanol (2.9 g, 67.1% yield) as a colorless oil. LC-MS (ESI) found:116 [M+H-56j.

Reference： [1]Patent: US2013/338190,2013,A1 .Location in patent: Paragraph 0037; 0038
[2]Patent: EP2684877,2014,A2 .Location in patent: Page/Page column 0032; 0033
[3]Patent: TWI524893,2016,B .Location in patent: Page/Page column 44; 45
[4]Patent: WO2018/31877,2018,A1 .Location in patent: Paragraph 00150

78
[ 3554-65-2 ]
(E)-N-[4-[[3-chloro-4-(2-pyridylmethoxy)phenyl]amino]-3-cyano-7-ethoxy-6-quinolyl]-3-[(2R)-1-methylpyrrolidin-2-yl]prop-2-enamide maleate [ No CAS ]

Reference： [1]Patent: EP2684877,2014,A2
[2]Patent: US2013/338190,2013,A1

79
[ 3554-65-2 ]
[ 1397922-62-1 ]

Reference： [1]Patent: EP2684877,2014,A2
[2]Patent: US2013/338190,2013,A1

80
[ 1616735-22-8 ]
[ 3554-65-2 ]
[ 1616735-31-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 4932 - 4940

81
[ 1616735-23-9 ]
[ 3554-65-2 ]
[ 1616735-37-5 ]

Reference： [1]Organic and Biomolecular Chemistry,2014,vol. 12,p. 4932 - 4940

82
ethyl (2R)-2-[(5Sa)-5-(3-chloro-4-hydroxy-2-methylphenyl)-6-(4-fluorophenyl)thieno[2,3-d]pyrimidin-4-yl]oxy-3-[2-(pyrazin-2-ylmethoxy)phenyl]propanoate [ No CAS ]
[ 3554-65-2 ]
C₄₁H₃₉ClFN₅O₅S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With di-tert-butyl-diazodicarboxylate; triphenylphosphine; In toluene; at 50℃;Inert atmosphere;	0.470 g ethyl (2R)-2-[(5Sj-5 -(3 -chloro-4-hydroxy-2-methyl-phenyl)-6-(4-fluorophenyl)thieno [2,3-d]pyrimidin-4-yl] oxy-3 - [2-(pyrazin-2-ylmethoxy)phenyl]propanoate (Preparation 6b) (0.7 mmol), 0.330 g 1-methylpiperidin-3- ol (2.0 mmol), and 0.524 g triphenyl phosphine (2.0 mmol) were dissolved in 15 mL drytoluene, then 0.46 1 g ditertbutyl azodicarboxylate (2.0 mmol) was added. The mixture was stirred at 50°C under nitrogen. During the reaction rearrangement of the methylpiperidine moiety was also observed. When no further conversion was observed, the volatiles were evaporated under reduced pressure, and the constitutional isomers were separated via flash chromatography using DCM and MeOH as eluents. The mixture of compounds elutingearlier were the precursors of Example 141 and 142, while the mixture of compounds eluting later were the precursors of Example 143, The obtained precursor derivatives were separately dissolved in dioxane-water 1:1 (10 mL/mmol) and 10 eq LiOH x 112° was added. The mixtures were stirred at room temperature until no further conversion was observed. Then they were individually diluted with brine, neutralized with 2 M HC1,extracted with DCM. The combined organic phases were dried over Na2SO4, filtered and concentrated under reduced pressure and purified separately via preparative reversed phase chromatography using 25 mM aqueous N11411C03 solution and MeCN as eluents to obtain Example 141 [HRMS calculated for C39H35C1FN5O5S: 739,203 1; found 740.2119 (M+H)], Example 142 [HRMS calculated for C39H35C1FN505S: 739.2031; found740.2088 (M+H)], and Example 143 [HRMS calculated for C391135C1FN505S: 739.2031; found 740.2101 and 740.2078 (M+H)1.

Reference： [1]Patent: WO2015/97123,2015,A1 .Location in patent: Page/Page column 260; 261

83
[ 55717-45-8 ]
[ 3554-65-2 ]
(R)-2-bromo-5-((1-methylpyrrolidin-2-yl)methoxy)pyridine [ No CAS ]

Reference： [1]MedChemComm,2016,vol. 7,p. 1580 - 1586

84
[ 3554-65-2 ]
[ 1269662-78-3 ]

Reference： [1]Patent: TWI524893,2016,B

85
[ 124-63-0 ]
[ 3554-65-2 ]
(1-methylpyrrolidin-2-yl)methyl methanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2 g	With triethylamine; In dichloromethane; at 20℃; for 1h;	Into a 50-mL round-bottom flask, was placed (l-methylpyrrolidin-2-yl)methanol (1 g, 8.68 mmol, 1 equiv), TEA (2.66 g, 26.29 mmol, 3.00 equiv), dichloromethane (10 mL), methanesulfonyl chloride (1.29 g, 11.26 mmol, 1.30 equiv). The resulting solution was stirred for 1 h at 20 °C. This resulted in 2 g (119percent) of the title compound as yellow oil.

Reference： [1]Patent: WO2017/181177,2017,A1 .Location in patent: Paragraph 0738-0740

86
[ 3554-65-2 ]
2-(2-methoxy-5-nitrophenoxymethyl)-1-methylpyrrolidine [ No CAS ]

Reference： [1]Patent: WO2017/181177,2017,A1

87
[ 3554-65-2 ]
4-methoxy-3-[(1-methylpyrrolidin-2-yl)methoxy]aniline [ No CAS ]

Reference： [1]Patent: WO2017/181177,2017,A1

88
[ 3554-65-2 ]
N2-(4-methoxy-3-((1-methylpyrrolidin-2-yl)methoxy)phenyl)-N4-methylpyrimidine-2,4-diamine [ No CAS ]

Reference： [1]Patent: WO2017/181177,2017,A1

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