[ CAS No. 2026-48-4 ]

Name: 2026-48-4|(S)-2-Amino-3-methylbutan-1-ol|97%
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Quality Control of [ 2026-48-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 2026-48-4 ]

Product Details of [ 2026-48-4 ]

CAS No. :	2026-48-4	MDL No. :
Formula :	-	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	NWYYWIJOWOLJNR-RXMQYKEDSA-N
M.W :	-	Pubchem ID :	640993
Synonyms :

Calculated chemistry of [ 2026-48-4 ]

Physicochemical Properties

Num. heavy atoms :	7
Num. arom. heavy atoms :	0
Fraction Csp3 :	1.0
Num. rotatable bonds :	2
Num. H-bond acceptors :	2.0
Num. H-bond donors :	2.0
Molar Refractivity :	30.02
TPSA :	46.25 Å²

Pharmacokinetics

GI absorption :	High
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) :	-6.93 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.43
Log Po/w (XLOGP3) :	0.0
Log Po/w (WLOGP) :	-0.04
Log Po/w (MLOGP) :	0.23
Log Po/w (SILICOS-IT) :	-0.21
Consensus Log Po/w :	0.28

Druglikeness

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

Water Solubility

Log S (ESOL) :	-0.35
Solubility :	46.3 mg/ml ; 0.449 mol/l
Class :	Very soluble
Log S (Ali) :	-0.52
Solubility :	31.0 mg/ml ; 0.3 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.15
Solubility :	73.4 mg/ml ; 0.711 mol/l
Class :	Soluble

Medicinal Chemistry

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

Safety of [ 2026-48-4 ]

Signal Word:		Class:
Precautionary Statements:		UN#:
Hazard Statements:		Packing Group:

Application In Synthesis of [ 2026-48-4 ]

* 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 [ 2026-48-4 ]
Downstream synthetic route of [ 2026-48-4 ]

[ 2026-48-4 ] Synthesis Path-Upstream 1~6

1
[ 2026-48-4 ]
[ 7533-40-6 ]

Reference： [1] New Journal of Chemistry, 2009, vol. 33, # 1, p. 181 - 185

2
[ 2026-48-4 ]
[ 77877-19-1 ]

Reference： [1] Tetrahedron Asymmetry, 2002, vol. 13, # 7, p. 675 - 680
[2] Chemische Berichte, 1996, vol. 129, # 11, p. 1361 - 1368
[3] Journal of Organic Chemistry, 1991, vol. 56, # 7, p. 2489 - 2498

3
[ 75-15-0 ]
[ 2026-48-4 ]
[ 76186-04-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium hydroxide In ethanol; water at 80℃; for 15 h; Inert atmosphere; Sealed tube	The following procedure gives a higher yield than that reported in the literature. Erik Galvez, P. R., Felix Urp. (2009) Preparation of (S)-4-Isopropyl-N-Propanoyl-l,3- Thiazolidine-2-Thione, Organic Syntheses 86, 70. A sealed tube was charged with a solution of KOH (2.7 g, 48.4 mmol, 5 equiv.) in 8 mL of water, 2 mL of EtOH, CS₂ (2.9 mL, 48.4 mmol, 5 equiv.), and (S)-(+)-2-amino-3 -methyl- 1-butanol (1.0 g, 9.69 mmol, 1 equiv.). The mixture was heated at 80 °C for 15 hours, purged with N₂ to remove the excess CS₂, and neutralized by adding aqueous HC1 solution (1 M). After extraction with EtOAc (3 x 60 mL) the organic layer was washed with brine (5 mL), dried over MgS0₄, and concentrated in vacuo. The residue was purified on a silica gel chromatography to give the desired product as a yellow solid (1.19 g, 76percent). The characterization data match with those in the literature.

Reference： [1] European Journal of Organic Chemistry, 2011, # 23, p. 4397 - 4408
[2] Organic Syntheses, 2009, vol. 86, p. 70 - 80
[3] Tetrahedron, 2008, vol. 64, # 24, p. 5637 - 5644
[4] Organic Letters, 2011, vol. 13, # 21, p. 5916 - 5919
[5] European Journal of Organic Chemistry, 2009, # 33, p. 5841 - 5846
[6] European Journal of Organic Chemistry, 2016, vol. 2016, # 4, p. 688 - 692
[7] European Journal of Organic Chemistry, 2017, vol. 2017, # 1, p. 29 - 33
[8] Journal of Organic Chemistry, 1995, vol. 60, # 20, p. 6604 - 6607
[9] Patent: WO2016/161168, 2016, A1, . Location in patent: Page/Page column 23; 24
[10] Journal of Organic Chemistry, 1986, vol. 51, # 12, p. 2391 - 2393
[11] Organic Letters, 2016, vol. 18, # 11, p. 2560 - 2563
[12] Phosphorus, Sulfur and Silicon and the Related Elements, 2015, vol. 190, # 1, p. 112 - 122
[13] Tetrahedron Letters, 2018, p. 624 - 627

4
[ 75-15-0 ]
[ 2026-48-4 ]
[ 76186-04-4 ]
[ 84272-19-5 ]

Reference： [1] Tetrahedron, 1994, vol. 50, # 24, p. 7283 - 7292

5
[ 2026-48-4 ]
[ 76186-04-4 ]

Reference： [1] Journal of Organic Chemistry, 1995, vol. 60, # 20, p. 6604 - 6607

6
[ 2026-48-4 ]
[ 28920-43-6 ]
[ 160885-98-3 ]

Yield	Reaction Conditions	Operation in experiment
86%	at 20℃; for 0.0333333 h; Sonication; Irradiation; Green chemistry	General procedure: Amine (1 mmol) and Fmoc-Cl (1.1 mmol) were placed in a glass tube under neat conditions and were sonicated for a suitable time (as indicated in Tables 1, 2 and 3). All reactions were performed in a water bath at room temperature. After completion of the reaction (as indicated by TLC), 5 cm3 of diethyl ether was added to the mixture. The N-Fmoc derivatives were crystallized and were obtained in good to excellent yields. Purification of the product was accomplished by recrystallization from diethyl ether.

Reference： [1] Journal of the Brazilian Chemical Society, 2016, vol. 27, # 3, p. 546 - 550
[2] Journal of Organic Chemistry, 1995, vol. 60, # 2, p. 405 - 410

[ 2026-48-4 ] Synthesis Path-Downstream 1~69

1
[ 1003-31-2 ]
[ 2026-48-4 ]
[ 149065-76-9 ]

Yield	Reaction Conditions	Operation in experiment
93%	With potassium carbonate; In ethylene glycol; glycerol; at 110℃; for 72h;Inert atmosphere;	K2CO3 (0.12 g, 0.1 equiv) and glycerol (5 ml) were charged into a Schlenk flask and placed under an argon atmosphere. To this was added nitrile 6B (1.0 g, 1.0 equiv), S-valinol (1.64 g, 1.7 equiv), and dry ethylene glycol (10 ml). The resulting clear colorless solution was heated to 110 C for 72 h to form a purple solution. This was cooled and quenched into satd aq NH4Cl (100 ml) before being extracted with Et2O (3 × 100 ml). The combined organic phase was dried (MgSO4) and the solvent evaporated to give a purple oil. This was purified by filtration through an alumina plug (washing with Et2O) to give a pale yellow oil (1.52 g, 93%).IR (NaCl, thin film): C-H 2959.4, CN 1651.5; MS (CI+, NH3): m/z = 196.2 (M+H+, 100%); 1H NMR (400 MHz, CDCl3) delta 7.51 (1H, dd, J = 3.7, 1.2 Hz, H3'), 7.35 (1H, dd, J = 5.0, 1.2 Hz, H5'), 6.98 (1H, dd, J = 5.0, 3.7 Hz, H4'), 4.31 (1H, td, J = 8.1, 1.2 Hz, H4), 3.96-4.12 (2H, m, H5), 1.79 (1H, pseudo sext, J = 13.1, 6.7, 6.7, 6.7, 6.7, 6.7 Hz, CH(CH3)2), 0.89 (6H, dd, J = 39.9, 6.8 Hz, CH(CH3)2); 13C NMR (100 MHz, CDCl3) delta ppm 159.4 (C2), 130.9 (C2'), 130.6 (C3'), 130.0 (C4'), 127.9 (C5'), 73.0 (C5), 70.8 (C4), 33.1 (CH(CH3)2), 19.4 (CH(CH3)2); CHN (C10H13NOS) found: C 61.35, H 6.84, N 7.55; required: C 61.50, H 6.71, N 7.17.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5120 - 5123
[2]Tetrahedron Letters,1993,vol. 34,p. 2015 - 2018
[3]Tetrahedron,1994,vol. 50,p. 799 - 808
[4]Journal of the Chemical Society. Perkin transactions I,1994,p. 2065 - 2072
[5]Synthesis,2004,p. 1879 - 1888
[6]Synlett,2004,p. 106 - 110
[7]Tetrahedron Asymmetry,2006,vol. 17,p. 2442 - 2447

2
[ 75-15-0 ]
[ 2026-48-4 ]
[ 76186-04-4 ]

Yield	Reaction Conditions	Operation in experiment
76%	With potassium hydroxide; In ethanol; water; at 80℃; for 15h;Inert atmosphere; Sealed tube;	The following procedure gives a higher yield than that reported in the literature. Erik Galvez, P. R., Felix Urp. (2009) Preparation of (S)-4-Isopropyl-N-Propanoyl-l,3- Thiazolidine-2-Thione, Organic Syntheses 86, 70. A sealed tube was charged with a solution of KOH (2.7 g, 48.4 mmol, 5 equiv.) in 8 mL of water, 2 mL of EtOH, CS2 (2.9 mL, 48.4 mmol, 5 equiv.), and (S)-(+)-2-amino-3 -methyl- 1-butanol (1.0 g, 9.69 mmol, 1 equiv.). The mixture was heated at 80 C for 15 hours, purged with N2 to remove the excess CS2, and neutralized by adding aqueous HC1 solution (1 M). After extraction with EtOAc (3 x 60 mL) the organic layer was washed with brine (5 mL), dried over MgS04, and concentrated in vacuo. The residue was purified on a silica gel chromatography to give the desired product as a yellow solid (1.19 g, 76%). The characterization data match with those in the literature.

Reference： [1]European Journal of Organic Chemistry,2011,p. 4397 - 4408
[2]Organic Syntheses,2009,vol. 86,p. 70 - 80
[3]Tetrahedron,2008,vol. 64,p. 5637 - 5644
[4]Organic Letters,2011,vol. 13,p. 5916 - 5919
[5]European Journal of Organic Chemistry,2009,p. 5841 - 5846
[6]European Journal of Organic Chemistry,2016,vol. 2016,p. 688 - 692
[7]European Journal of Organic Chemistry,2017,vol. 2017,p. 29 - 33
[8]Journal of Organic Chemistry,1995,vol. 60,p. 6604 - 6607
[9]Patent: WO2016/161168,2016,A1 .Location in patent: Page/Page column 23; 24
[10]Journal of Organic Chemistry,1986,vol. 51,p. 2391 - 2393
[11]Organic Letters,2016,vol. 18,p. 2560 - 2563
[12]Phosphorus, Sulfur and Silicon and the Related Elements,2015,vol. 190,p. 112 - 122
[13]Tetrahedron Letters,2018,p. 624 - 627

3
[ 65007-00-3 ]
[ 2026-48-4 ]
[ 201230-82-2 ]
[ 140706-16-7 ]

Reference： [1]Tetrahedron Letters,1992,vol. 33,p. 1181 - 1184

4
[ 75-15-0 ]
[ 2026-48-4 ]
[ 76186-04-4 ]
[ 84272-19-5 ]

Reference： [1]Tetrahedron,1994,vol. 50,p. 7283 - 7292

5
[ 2026-48-4 ]
[ 34825-99-5 ]
[ 148461-14-7 ]

Reference： [1]Recueil des Travaux Chimiques des Pays-Bas,1995,vol. 114,p. 206 - 210

6
[ 2026-48-4 ]
[ 64419-24-5 ]
[ 169171-35-1 ]

Reference： [1]Journal of the American Chemical Society,1995,vol. 117,p. 8312 - 8321

7
[ 2026-48-4 ]
[ 25309-39-1 ]
[ 172041-77-9 ]

Reference： [1]Tetrahedron Asymmetry,1995,vol. 6,p. 2487 - 2494

8
[ 2026-48-4 ]
[ 471-46-5 ]
[ 133464-02-5 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 3375 - 3389

9
[ 1620-75-3 ]
[ 2026-48-4 ]
2-((S)-4-Isopropyl-4,5-dihydro-oxazol-2-yl)-6-methyl-pyridine [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1997,vol. 8,p. 3183 - 3184

10
[ 4513-94-4 ]
[ 2026-48-4 ]
(4S)-2-(pyrrol-2-yl)-4-isopropyl-4,5-dihydrooxazole [ No CAS ]

Reference： [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1998,vol. 53,p. 476 - 480

11
[ 2026-48-4 ]
[ 36057-44-0 ]
(S)-2-<4,5-dihydro-4-(1-methylethyl)oxazol-2-yl>-4-methoxypyridine [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,1999,vol. 10,p. 1457 - 1464

12
[ 2893-33-6 ]
[ 2026-48-4 ]
[ 118949-61-4 ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 6389 - 6396
[2]Synlett,2005,p. 2321 - 2324
[3]Journal of the American Chemical Society,2016,vol. 138,p. 4722 - 4725
[4]Tetrahedron Asymmetry,1999,vol. 10,p. 3803 - 3809

13
[ 2893-33-6 ]
[ 2026-48-4 ]
[ 118949-61-4 ]
(S)-2-cyano-6-[4,5-dihydro-4-(1-methylethyl)oxazol-2-yl]pyridine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 6389 - 6396
[2]Tetrahedron Asymmetry,1999,vol. 10,p. 3803 - 3809
[3]Synlett,2005,p. 2321 - 2324

14
[ 2026-48-4 ]
[ 617-36-7 ]
[ 234443-57-3 ]

Reference： [1]Helvetica Chimica Acta,2001,vol. 84,p. 3178 - 3196
[2]Organic Letters,1999,vol. 1,p. 141 - 144
[3]Chemistry - A European Journal,2015,vol. 21,p. 17503 - 17507

15
[ 41731-83-3 ]
[ 2026-48-4 ]
ethyl 2-(1-hydroxymethyl-2-methylpropylamino)-1,3-thiazole-5-carboxylate [ No CAS ]

Reference： [1]Journal of Heterocyclic Chemistry,2003,vol. 40,p. 353 - 356

16
[ 2026-48-4 ]
[ 39234-86-1 ]
[ 652150-79-3 ]

Reference： [1]Journal of the American Chemical Society,2004,vol. 126,p. 14 - 15

17
[ 2026-48-4 ]
[ 7321-55-3 ]
[ 131833-92-6 ]

Reference： [1]Synlett,2005,p. 2321 - 2324
[2]Heterocycles,2012,vol. 86,p. 203 - 217

18
[ 2026-48-4 ]
[ 2305-32-0 ]
(1S,2S)-Cyclohexane-1,2-dicarboxylic acid bis-[((S)-1-hydroxymethyl-2-methyl-propyl)-amide] [ No CAS ]
(1R,2R)-Cyclohexane-1,2-dicarboxylic acid bis-[((S)-1-hydroxymethyl-2-methyl-propyl)-amide] [ No CAS ]

Reference： [1]Canadian Journal of Chemistry,2004,vol. 82,p. 306 - 313

19
[ 2026-48-4 ]
[ 37091-73-9 ]
1,3-dimethyl-2-[(S)-1-hydroxymethyl-2-methylpropylimino]imidazolidine [ No CAS ]

Reference： [1]Journal of Organic Chemistry,2000,vol. 65,p. 7770 - 7773

20
[ 2026-48-4 ]
[ 19715-19-6 ]
[ 372137-88-7 ]

Reference： [1]Journal of Organometallic Chemistry,2006,vol. 691,p. 2228 - 2236

21
[ 2026-48-4 ]
[ 34374-88-4 ]
C₂₄H₃₉N₃O₆ [ No CAS ]

Reference： [1]Tetrahedron Asymmetry,2007,vol. 18,p. 2820 - 2827

22
[ 2026-48-4 ]
[ 118949-61-4 ]

Reference： [1]Synthesis,2006,p. 2996 - 3002

23
[ 2026-48-4 ]
[ 131833-89-1 ]

Reference： [1]Journal of Organic Chemistry,1997,vol. 62,p. 3375 - 3389
[2]Helvetica Chimica Acta,1991,vol. 74,p. 232 - 240
[3]Tetrahedron Asymmetry,2011,vol. 22,p. 797 - 811

24
[ 2026-48-4 ]
[ 183990-64-9 ]

Reference： [1]Tetrahedron Asymmetry,1996,vol. 7,p. 2911 - 2922

25
[ 2026-48-4 ]
[ 148461-14-7 ]

Reference： [1]Tetrahedron,1996,vol. 52,p. 7547 - 7583
[2]Tetrahedron,1996,vol. 52,p. 7547 - 7583
[3]Tetrahedron,1994,vol. 50,p. 799 - 808
[4]Tetrahedron Letters,1993,vol. 34,p. 3149 - 3150

26
[ 2026-48-4 ]
[ 76186-04-4 ]

Reference： [1]Journal of Organic Chemistry,1995,vol. 60,p. 6604 - 6607

27
[ 2026-48-4 ]
[ 172695-33-9 ]

Reference： [1]Tetrahedron,1995,vol. 51,p. 12337 - 12350

28
[ 2766-74-7 ]
[ 55854-46-1 ]
5-thiophene-2-sulfonyl chloride [ No CAS ]
[ 2026-48-4 ]
5-chloro-N-[(1S)-1-(hydroxymethyl)-2-methylpropyl]thiophene-2-sulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In tetrahydrofuran; methanol;	Example 8 5-Chloro-N-[(1S)-1-(hydroxymethyl)-2-methylpropyl]thiophene-2-sulfonamide To a solution of L-valinol (25.8 mg, 0.25 mmol) in THF (3 mL) was added triethylamine (58 muL, 0.3 mmol) and 5-chlorothiophene-2-sulfonyl chloride (54 mg, 0.25 mmol). The solution was stirred for 8 to 16 h, then concentrated. The residue was dissolved in MeOH (1.5 mL) and purified by semi-preparative RP-HPLC1 to give Example 8 (19.5 mg). The following compounds (Examples 8-10, Table 2) were prepared using 5-thiophene-2-sulfonyl chloride and 5-bromothiophenesulfonyl chloride with L-valinol and D-valinol and following the procedure outlined in Example 8.

Reference： [1]Patent: US2002/183361,2002,A1

29
[ 4630-82-4 ]
[ 2026-48-4 ]
[ 475571-12-1 ]

Yield	Reaction Conditions	Operation in experiment
60%	Zn4(OAc)6O; In chlorobenzene; for 12h;Heating / reflux;Product distribution / selectivity;	Examples 2 to 32 (Production of Oxazolines); According to the following scheme: [Show Image] (wherein R and R' represent a functional group shown in Table 1 below), the reaction was carried out in the same manner as in Example 1 except that esters and carboxylic acids shown in Table 1 were used in place of methyl benzoate in Example 1, and metal compounds shown in Table 1 were used in place of Zn4(OCOCF3)6O. The yields of the resulting oxazolines are shown in Table 1. The number of moles of each of the substrates (esters and carboxylic acids) used in Examples 16 to 32 is 3 mmol. In Table, symbol Ph represents a phenyl group, symbol Cy represents a cyclohexyl group, symbol Bu represents a butyl group, symbol Me represents a methyl group, symbol Et represents an ethyl group, symbol Boc represents a t-butoxycarbonyl group, symbol Bn represents a benzyl group, symbol Ac represents an acetyl group, symbol MEM represents methoxyethoxymethyl, and symbol TBDMS represents a t-butyldimethylsilyl group (these definitions hereinafter apply).
51%	Zn4(OCOCF3)6O; In chlorobenzene; for 12h;Heating / reflux;Product distribution / selectivity;	Examples 2 to 32 (Production of Oxazolines); According to the following scheme: [Show Image] (wherein R and R' represent a functional group shown in Table 1 below), the reaction was carried out in the same manner as in Example 1 except that esters and carboxylic acids shown in Table 1 were used in place of methyl benzoate in Example 1, and metal compounds shown in Table 1 were used in place of Zn4(OCOCF3)6O. The yields of the resulting oxazolines are shown in Table 1. The number of moles of each of the substrates (esters and carboxylic acids) used in Examples 16 to 32 is 3 mmol. In Table, symbol Ph represents a phenyl group, symbol Cy represents a cyclohexyl group, symbol Bu represents a butyl group, symbol Me represents a methyl group, symbol Et represents an ethyl group, symbol Boc represents a t-butoxycarbonyl group, symbol Bn represents a benzyl group, symbol Ac represents an acetyl group, symbol MEM represents methoxyethoxymethyl, and symbol TBDMS represents a t-butyldimethylsilyl group (these definitions hereinafter apply).

Reference： [1]Patent: EP1958940,2008,A1 .Location in patent: Page/Page column 18-19
[2]Patent: EP1958940,2008,A1 .Location in patent: Page/Page column 18-19

30
[ 2026-48-4 ]
[ 17191-43-4 ]
[ 944281-90-7 ]

Yield	Reaction Conditions	Operation in experiment
91%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 18h;	After 422 mg (2.2 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 555 mg (2 mmol) of 1-[[(phenylmethoxy)carbonyl]amino]cyclohexanecarboxylic acid, 322 mg (2.1 mmol) of 1-hydroxybenzotriazole and 206 mg (2 mmol) of L-valinol in 20 ml of methylene chloride under ice-cooling, the mixture was stirred at room temperature for 18 hours. The reaction solution was concentrated under reduced pressure, ethyl acetate was added to the residue, and the mixture was washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine. The organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 662 mg (91%) of the title compound.1H-NMR (CDCl3, delta): 0.87 (3H, d, J=7 Hz), 0.92 (3H, d, J=7 Hz), 1.28-1.46 (3H, m), 1.52-1.70 (3H, m), 1.73-1.82 (1H, m), 1.85-2.03 (4H, m), 2.76 (1H, br-s), 3.42-4.47 (1H, m), 3.65-3.74 (2H, m), 5.02-5.16 (3H, m), 6.36 (1H, d, J=8 Hz), 7.30-7.40 (5H, m)
91%	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 18h;	Reference Example 132 N-[[1-[[(Phenylmethoxy)carbonyl]amino]cyclohexyl]carbonyl]-L-valinol After 422 mg (2.2 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 555 mg (2 mmol) of 1-[[(phenylmethoxy)carbonyl]amino]cyclohexanecarboxylic acid, 322 mg (2.1 mmol) of 1-hydroxybenzotriazole and 206 mg (2 mmol) of L-valinol in 20 ml of methylene chloride under ice-cooling, the mixture was stirred at room temperature for 18 hours. The reaction solution was concentrated under reduced pressure, ethyl acetate was added to the residue, and the mixture was washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine. The organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 662 mg (91%) of the title compound. 1H-NMR (CDCl3, delta): 0.87 (3H, d, J=7Hz), 0.92 (3H, d, J=7Hz), 1.28-1.46 (3H, m), 1.52-1.70 (3H, m), 1.73-1.82 (1H, m), 1.85-2.03 (4H, m), 2.76 (1H, br-s), 3.42-4.47 (1H,m), 3.65-3.74 (2H, m), 5.02-5.16 (3H, m), 6.36 (1H, d, J=8Hz), 7.30-7.40 (5H, m)
	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 - 20℃; for 18h;	REFERENCE EXAMPLE 178N-[[1-[[(Phenylmethoxy)carbonyl]amino]cyclohexyl]carbonyl]-L-valinol Under ice-cooling, 422 mg (2.2 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride was added to a solution of 555 mg (2 mmol) of 1-[[(phenylmethoxy)carbonyl]amino]cyclohexanecarboxylic acid, 322 mg (2.1 mmol) of 1-hydroxybenzotriazole and 206 mg (2 mmol) of L-valinol in 20 ml of methylene chloride, and thereafter the mixture was stirred at room temperature for 18 hours. The reaction solution was concentrated under reduced pressure, ethyl acetate was added to the residue, and the mixture was washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and then saturated brine. The organic layer was dried with anhydrous sodium sulfate and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography to obtain 662 mg (91) of the title compound.1H-NMR (CDCl3, delta): 0.87 (3H, d, J=7 Hz), 0.92 (3H, d, J=7 Hz), 1.28-1.46 (3H, m), 1.52-1.70 (3H, m), 1.73-1.82 (1H, m), 1.85-2.03 (4H, m), 2.76 (1H, br-s), 3.42-4.47 (1H, m), 3.65-3.74 (2H, m), 5.02-5.16 (3H, m), 6.36 (1H, d, J=8 Hz), 7.30-7.40 (5H, m)

Reference： [1]Patent: US2009/111983,2009,A1 .Location in patent: Page/Page column 62
[2]Patent: EP1975162,2008,A1 .Location in patent: Page/Page column 85-86
[3]Patent: US2009/137799,2009,A1 .Location in patent: Page/Page column 62; 63

31
[ 18791-98-5 ]
[ 2026-48-4 ]
[ 1013926-20-9 ]

Reference： [1]Organic and Biomolecular Chemistry,2008,vol. 6,p. 562 - 566

32
[ 30148-21-1 ]
[ 2026-48-4 ]
[ 1026258-90-1 ]

Reference： [1]Organic and Biomolecular Chemistry,2009,vol. 7,p. 229 - 231

33
[ 2026-48-4 ]
[ 83-40-9 ]
[ 1104058-34-5 ]

Reference： [1]Angewandte Chemie - International Edition,2008,vol. 47,p. 9125 - 9129

34
[ 2739-74-4 ]
[ 2026-48-4 ]
[ 1176200-56-8 ]

Reference： [1]Organic Letters,2009,vol. 11,p. 3398 - 3401

35
[ 412319-88-1 ]
[ 2026-48-4 ]
[ 28314-83-2 ]
2-(5-bromo-2,4-difluorobenzoyl)-3-((S)-1-hydroxymethyl-2-methylpropylmethylamino)acrylic acid ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Example 2-2: Production of crystal form II of the compound A; Step 1; 5-Bromo-2,4-difluorobenzoic acid (82.7 kg, 349 mol) was dissolved in toluene (420 L), thionyl chloride (62.3 kg, 523 mol) and dimethylformamide (catalytic amount) were added, and the mixture was stirred at 70C for 6 hr. The reaction mixture was allowed to cool to room temperature, concentrated under reduced pressure, and azeotroped again with toluene (420 L). The residue was dissolved in toluene (220 L), this solution was added dropwise to a solution of ethyl 3,3-dimethylaminoacrylate (55.0 kg, 384 mol) and diisopropylethylamine (58.6 kg, 523 mol) in toluene (220 L), and the mixture was stirred with heating at 70C for 21 hr. The reaction mixture was allowed to cool to room temperature, (S) - (+) -valinol (36.0 kg, 349 mol) was added, and the mixture was stirred at room temperature for 1.5 hr. Water (420 L) was added to the reaction mixture to allow partitioning, and the organic layer was washed successively with 1N hydrochloric acid (250 L, twice), water (420 L), 5% aqueous sodium hydrogen carbonate (250 L, twice), water (420 L) and 10% brine (250 L). The extract was concentrated under reduced pressure and azeotroped with dimethylformamide (420 L) to give a concentration residue (330 L) containing a crude product of 2- (5-bromo-2,4-difluorobenzoyl)-3-((S)-l-hydroxymethyl-2- methylpropylmethylamino) acrylic acid ethyl ester.

Reference： [1]Patent: WO2005/113508,2005,A1 .Location in patent: Page/Page column 28-29

36
[ 2026-48-4 ]
[ 98873-55-3 ]
[ 1210068-56-6 ]

Reference： [1]Journal of Organometallic Chemistry,2010,vol. 695,p. 195 - 200

37
[ 2026-48-4 ]
[ 129298-23-3 ]
[ 1197180-67-8 ]

Reference： [1]Journal of the American Chemical Society,2009,vol. 131,p. 16678 - 16680

38
[ 2026-48-4 ]
[ 2903-46-0 ]
C₁₅H₂₂N₂O₃ [ No CAS ]

Reference： [1]Chemical Communications,2010,vol. 46,p. 6822 - 6824

39
[ 2026-48-4 ]
[ 55309-58-5 ]
[ 118949-61-4 ]

Reference： [1]Tetrahedron Asymmetry,2010,vol. 21,p. 1221 - 1225

40
[ 960613-96-1 ]
[ 2026-48-4 ]
[ 1269646-86-7 ]

Yield	Reaction Conditions	Operation in experiment
99%	With N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 100℃; for 4h;	To a solution of (S)-2-amino-3-methylbutan-l-ol (3.3 g, 32 mmol) inDMF was added 3-bromo-5-chloropyrazolo[l,5-a]pyrimidine (2.5 g, 11 mmol) and N-ethyl- N-isopropylpropan-2-amine (4.2 g, 32 mmol) and the reaction was heated to 100 C for 4 hours. The reaction mixture was poured into EtOAc and washed with water and brine, dried over magnesium sulfate and concentrated in vacuo to yield (S)-2-(3-bromopyrazolo[l,5- a]pyrimidin-5-ylamino)-3-methylbutan-l-ol (3.2g, 99%). LCMS (APCI+) m/z 299, 301 [M+H]+.

Reference： [1]Patent: WO2011/29027,2011,A1 .Location in patent: Page/Page column 64; 65

41
[ 2026-48-4 ]
[ 39775-31-0 ]
[ 1309959-98-5 ]

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2844 - 2848

42
[ 122918-25-6 ]
[ 2026-48-4 ]
[ 1304495-90-6 ]

Reference： [1]Green Chemistry,2011,vol. 13,p. 983 - 990

43
[ 122918-25-6 ]
[ 2026-48-4 ]
[ 819083-98-2 ]

Reference： [1]Green Chemistry,2011,vol. 13,p. 983 - 990

44
[ 29270-56-2 ]
[ 2026-48-4 ]
[ 874894-52-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With triethylamine; In N,N-dimethyl-formamide; at 23℃; for 2.5h;Darkness; Inert atmosphere;	To a vial containing NBD-F 2 (53.3 mg, 0.2911 mmol, 1.0 equiv) was added L-valinol5 14 (32.5 mg, 0.315 mmol, 1.1 equiv), 0.5 mL DMF, and then triethylamine (0.08 mL, 0.574 mmol, 2.0 equiv), immediately producing a black reaction mixture. The reaction was allowed to stir in the dark at 23 C for 2.5 h. The solvent was removed in vacuo with gentle heating (from 23 C to 70 C) to yield a black sludge which was then loaded onto a silica column using the dry-loading technique (see above). Flash column chromatography of the residue on silica gel (gradient used: DCM, then 15:1 DCM/MeOH) afforded the desired product 22 as a red film (74 mg, 95%). Rf (3:1 DCM/MeOH) = 0.83. 1H NMR (CDCl3, 500 MHz) delta: 8.45 (1H, d, J = 8.5 Hz), 6.59 (1H, br d, J = 9.5 Hz), 6.27 (1H, d, J = 8.9 Hz), 3.94 (2H, m), 3.69 (1H, br), 2.16 (1H, m, J = 6.7 Hz), 1.08 (3H, d, J = 9.2), 1.07 (3H, d, J = 9.2 Hz). HRMS (ES+): calcd for C11H15N4O4 [M+H]+ 267.1093, found 267.1097.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 2533 - 2535

45
[ 2026-48-4 ]
[ 13589-71-4 ]
[ 1104058-34-5 ]

Yield	Reaction Conditions	Operation in experiment
78%	With zinc(II) chloride; In chlorobenzene; at 131.0℃; for 72.0h;Inert atmosphere;	ZnCl2 (2.18 g, 0.1 equiv) was charged into a 250 ml Schlenk flask and heated under vacuum until molten (heatgun) before being allowed to cool under an argon atmosphere. S-valinol (23.92 g, 1.5 equiv) and nitrile 1B (20.58 g, 1.0 equiv) were dissolved in chlorobenzene (100 ml) and charged into the flask in one go. The resulting dark red solution was heated to 131 C for 72 h, before being cooled and the solvent was evaporated. The resulting dark oil was quenched into 2 M HCl (200 ml) and extracted with CH2Cl2 (5 × 100 ml). The combined organic phase was washed with H2O (100 ml) which was back-extracted with CH2Cl2 (2 × 50 ml). The combined organic phase was dried (MgSO4) and the solvent evaporated to give a dark red oil (31.48 g). This was purified by flash chromatography (product adhered to silica, eluting with 1:9 EtOAc in hexane, Rf = 0.73) to yield the title compound as a pale orange oil which slowly crystallized on standing (26.50 g, 78%). IR (ATR): Ar-H 2958.3, CN 1635.3; MS (CI+, NH3): m/z = 220 (M+H+, 100%); 1H NMR (400 MHz, CDCl3) delta ppm 12.59 (1H, br s, OH), 7.49 (1H, dd, J = 7.8, 1.6 Hz, H5), 7.23 (1H, dd, J = 7.3, 0.8 Hz, H3), 6.77 (1H, pent, J = 7.6 Hz, H4), 4.37-4.46 (1H, m, H4'), 4.06-4.17 (2H, m, H5'), 2.29 (3H, s, CH3), 1.79 (1H, dq, J = 13.3, 6.7 Hz, CH(CH3)2), 0.98 (6H, dd, J = 28.6, 6.5 Hz, CH(CH3)2); 13C NMR (100 MHz, CDCl3) delta 165.8 (C2'), 158.7 (COH), 134.6 (C5), 126.1 (C6), 125.9 (C3), 118.4 (C4), 110.3 (C2), 71.9 (C5'), 70.3 (C4'), 33.5 (CH(CH3)2), 19.1 (CH(CH3)2), 16.3 (CH3); CHN (C13H17NO2) found: C 71.21, H 7.81, N 6.42; required: C 71.21, H 7.81, N 6.39.

Reference： [1]Tetrahedron Letters,2011,vol. 52,p. 5120 - 5123

46
[ 2026-48-4 ]
[ 40856-59-5 ]
[ 1403598-22-0 ]

Reference： [1]European Journal of Organic Chemistry,2012,p. 4283 - 4286

47
[ 2026-48-4 ]
[ 328-89-2 ]
C₁₃H₁₅BrF₃NO₂ [ No CAS ]

Reference： [1]Organometallics,2012,vol. 31,p. 6933 - 6946,14

48
[ 2026-48-4 ]
[ 1483-56-3 ]
C₁₃H₁₅BrF₃NO₂ [ No CAS ]

Reference： [1]Organometallics,2012,vol. 31,p. 6933 - 6946,14

49
[ 2026-48-4 ]
[ 347-84-2 ]
[ 23096-47-1 ]
2-(4-fluorophenyl)-5-isopropyl-3-phenyl-1H-pyrrole [ No CAS ]

Reference： [1]Organic Letters,2013,vol. 15,p. 1436 - 1439

50
[ 2026-48-4 ]
[ 157402-44-3 ]
[ 1509929-20-7 ]

Reference： [1]Organometallics,2014,vol. 33,p. 194 - 205

51
[ 1198-30-7 ]
[ 2026-48-4 ]
(S)-4-isopropyl-2-(isoquinolin-1-yl)-4,5-dihydrooxazole [ No CAS ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2250 - 2253

52
[ 2026-48-4 ]
[ 1206227-46-4 ]

Reference： [1]Advanced Synthesis and Catalysis,2015,vol. 357,p. 2132 - 2142
[2]Phosphorus, Sulfur and Silicon and the Related Elements,2017,vol. 192,p. 555 - 559

53
[ 50-00-0 ]
[ 2026-48-4 ]
[ 2227-98-7 ]
(2S)-2-[({4-amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]-3-methylbutan-1-ol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	In water; tert-butyl alcohol; at 70℃; for 16h;Inert atmosphere;	[0047] Example G. Synthesis of (2S)-2-[({4-amino-5H-pyrrolo[3,2-d]pyrimidin-7- yljmethyl) amino] -3-methylbutan-l-ol (G. l). (0079) [0048] (2S)-2-[({4-Amino-5H-pyrrolo[3,2-d]pyrimidin-7-yl}methyl)amino]-3- methylbutan-l-ol (G.l). (2S)-2-Amino-3-methylbutan-l-ol (0.100 g, 0.97 mmol) 9- <strong>[2227-98-7]deazaadenine</strong> (0.130 g, 0.97 mmol), and aq. formaldehyde solution (37%, 0.087 mL, 1.16 mmol) were stirred in tert-butanol (3 mL) at 70 C for 16 h. Silica gel was added to absorb all the solvent then the solvent was evaporated and the residue purified by chromatography on silica gel (CHC13-7M NH3/MeOH, 93:7 then 85: 15) to give G.l as a colourless solid (0.082 g, 34%). XH NMR (500 MHz, CD3OD): delta 8.16 (s, IH), 7.47 (s, IH), 3.99 (d, J = 13.6 Hz, IH), 3.95 (d, J = 13.6 Hz, IH), 3.68 (dd, J = 11.3, 4.8 Hz, IH), 3.54 (dd, J = 11.3, 6.5 Hz, IH), 2.49 (m, IH), 1.90 (m, IH), 0.93 (d, J= 6.9 Hz, 3H), 0.88 (d, J= 6.9 Hz, 3H). 13C NMR (125.7 MHz, CD3OD, centre line delta 49.0): delta 152.1 (C), 150.8 (CH), 146.7 (C), 129.0 (CH), 115.4 (C), 115.0 (C), 64.6 (CH2), 62.3 (CH), 41.9 (CH), 29.8 (CH2), 19.2 (CH3), 18.9 (CH3). ESI-HRMS calcd for Ci2H20N5O+ (M+H)+, 250.1663, found 250.1661.

Reference： [1]Patent: WO2015/123101,2015,A1 .Location in patent: Paragraph 0047; 0048
[2]Journal of the American Chemical Society,2015,vol. 137,p. 14275 - 14280

54
[ 2026-48-4 ]
[ 2903-46-0 ]
C₁₅H₂₆N₂O [ No CAS ]

Reference： [1]Organic Letters,2016,vol. 18,p. 952 - 955

55
[ 2893-33-6 ]
[ 2026-48-4 ]
(S)-2-cyano-6-[4,5-dihydro-4-(1-methylethyl)oxazol-2-yl]pyridine [ No CAS ]

Reference： [1]Chemistry - A European Journal,2016,vol. 22,p. 6389 - 6396

56
[ 2026-48-4 ]
[ 347-84-2 ]
2-(4-fluorophenyl)-5-isopropyl-3-phenyl-1H-pyrrole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
35%Spectr.	With [Rh(OH)(cod)]2; C22H33BrN4(2+)*2Br(1-); sodium hydroxide; In para-xylene; at 125℃; for 6h;Schlenk technique; Inert atmosphere; Cooling with liquid nitrogen;	The following methodwas prepared trisubstituted pyrrole (4 '). As described above, trisubstitutedpyrrole (4 ') is atorvastatin is hyperlipidemic agent (trade name: Lipitor) isa compound that can be utilized as synthetic intermediates. The reaction schemeis shown in Table 9 ( "mol%" in the reaction scheme is ratiovalinol.).Sodium hydroxide in aSchlenk (0.40mmol), [Rh (OH) (cod)] 2 (0.005mmol), bis-NHC ligand (0.01mmol)and p- xylene (1ml) added and the mixture It was prepared. Then, a Schlenkcooled with liquid nitrogen and freeze-deaerated, and then attached one litercondensing gas bag filled with argon gas was filled to the Schlenk with argongas. Thereafter, the mixture was stirred at room temperature for 2 hours. Afterstirring, valinol and (1 mmol) and ketone (3 ') (2mmol) was added to the abovemixture and stirred for 6 hours at 125 C.After completion ofthe reaction, the reaction mixture was washed with saturated NH4Cl aqueoussolution, and the aqueous layer was extracted 3 times with CH 2 Cl 2.Then, in the same procedure as in Experimental Example 1-A1, the extract ispurified, it is the object product To give the trisubstituted pyrrole (4 ').Three yields of substituted pyrrole (4 ') (%) was measured by the same methodas Experimental Example 1 (entry 2).
23%Spectr.	With lithium hydride; In para-xylene; at 165℃; for 60h;Schlenk technique; Inert atmosphere; Cooling with liquid nitrogen;	The gas which has beendried by heating in a Schlenk heat gun was replaced with argon gas. It was thenadded NaOH (0.40mmol) at room temperature. In addition valinol the (1mmol) andpropiophenone (2mmol) and p- xylene (1ml) was added, to prepare a suspensionsolution. The Schlenk was cooled with liquid nitrogen and freeze-deaerated, andthen attached one liter condensing gas bag filled with argon gas was filled tothe Schlenk with argon gas.The mixture wassubjected to reaction and then stirred for 6 hours at 165 C. After completionof the reaction, the reaction mixture was washed with saturated NH4Cl aqueoussolution, and the aqueous layer was extracted 3 times with CH 2 Cl 2.Thereafter, the same procedure as in Experimental Example 1-A1, and the extractwas purified to give the pyrrole an object product (entry 1). Also, instead ofNaOH, except for using an alkali metal base in Table 3 described, in the samemanner as above to give the pyrrole (entry 2-6). Table 3 shows the results.
41%Spectr.	With C36H54Cl2N2P2Ru; potassium tert-butylate; In toluene; at 165℃; for 24h;Schlenk technique; Inert atmosphere;	A stirrer, a ruthenium complex (Compound 2c; RUPCY2) (7.5 mg, 0.01 mmol), potassium tert-butoxide (44.9 mg, 0.4 mmol), benzil-4-fluoro phenyl ketone (429 mg, 2.0 mmol), toluene (1.0 mL), and L-Valinol (0.11 mL, 1.0 mmol) were added to a 10-mL Young-Schlenk container that had been dried under reduced pressure and substituted with nitrogen. Thereafter, the mixture was reacted for 24 hours in a constant-temperature bath at 165 C. After the reaction was completed, a 1.5-M hydrogen chloride-methanol solution (400 muL) was added to the mixture, and then 1-phenyl-1-propanol was added as a standard substance. 1H NMR measurement was performed using a deuterated chloroform solvent. As a result, the target product, i.e., 2-(4-fluorophenyl)-5-isopropyl-3-phenyl-1H-pyrrole was obtained at an NMR yield of 41%

Reference： [1]Patent: JP5678438,2015,B2 .Location in patent: Paragraph 0086-0090
[2]Patent: JP5678438,2015,B2 .Location in patent: Paragraph 0091-0092
[3]Patent: US9463451,2016,B2 .Location in patent: Page/Page column 43

57
[ 2026-48-4 ]
[ 102359-00-2 ]
C₁₄H₁₈N₂O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		General procedure: A solution of 9a-d (2 mmol), EDCI (3 mmol) and HOBt (3 mmol) in dry DCM (20 mL) was stirred at 0C for 3.5 h. Then different substituted amines (2.2 mmol) and DIPEA (4 mmol) were added and the reaction was stirred at r.t. for another 1.5 h. The organic layer was washed with water and brine and dried over Na2SO4. Removal of the solvent gave a residue that was purified by column chromatography (silica gel, CH2Cl2-MeOH 100: 1 as an eluent) to furnish 10a-n as white solids.

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 3500 - 3511

58
[ 2026-48-4 ]
[ 142770-42-1 ]
(S)-1-((1-hydroxy-3-methylbutan-2-yl)amino)-4-propoxy-9H-thioxanthen-9-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
10.12%	With copper(l) iodide; potassium carbonate; In methanol; at 100℃; for 48h;	General procedure: 1-Chloro-4-propoxy-9H-thioxanthen-9-one (Tx, 450 mg, 1.48 mmol) and a suitable chiral aminoalcohol (9-16, 1.72 mmol) were dissolved in methanol (30 mL) and CuI (0.15 mmol) and K2CO3(1.92 mmol) were added. The reaction mixture was heated at 100 C in a muffle furnace for 48 h.After the completion of the reaction, the crude material was filtrated, washed with dichloromethane,and the organic solvents were evaporated under reduced pressure. Then, the obtained solid wasdissolved in 50 mL of dichloromethane and extracted with HCl 1M(3 50 mL). The aqueous layer wasbasified with NaOH 20% and extracted with dichloromethane (3 100 mL). The organic layers weregathered, washed with water (3 50 mL), dried over anhydrous sodium sulphate and the solvent wasevaporated under reduced pressure. Then, a solid phase extraction using a cation exchange cartridgeDiscovery DSC-SCX was applied to further purify the extracted material. First, an activation ofthe cartridge with dichloromethane (50 mL) was performed followed by loading the cartridge withthe sample (previously incorporated in silica). Then, elution was carried out with the followingsolvents: dichloromethane, a mixture of dichloromethane/methanol 5:5 (v/v), methanol 100% andNH3 2% in methanol. The fractions containing the chiral ATxs were gathered and the solvent wasevaporated under reduced pressure. A flash column chromatography with n-hexane/ethyl acetate ingradient and crystallization from chloroform and petroleum ether (4:1) were also performed to obtainpure compounds.

Reference： [1]Molecules,2018,vol. 23

59
[ 2026-48-4 ]
[ 214630-00-9 ]
(3R)-7-hydroxy-N-[(1S)-1-(hydroxymethyl)-2-methylpropyl]-1,2,3,4-tetrahydroisoquinoline-3-carboxamide hydrochloride [ No CAS ]

Reference： [1]Patent: WO2018/53222,2018,A1

60
[ 2026-48-4 ]
[ 214630-00-9 ]
tert-butyl (3R)-7-hydroxy-3-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamoyl}-1,2,3,4-tetrahydroisoquinoline-2-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
72%	With benzotriazol-1-ol; triethylamine; dicyclohexyl-carbodiimide; In tetrahydrofuran; at 20℃; for 72h;Cooling with ice;	A solution of L-valinol (prepared according to literature method: J. (0257) Org. Chem. 65, 5037-5042) (2.0 g, 19 mmol), Boc-7-hydroxy-D-Tic (5.0 g, 17 mmol), and HOBt (0258) (2.3 g, 17 mmol) in THF (60 mL) in an ice bath was treated with a solution of DCC (4.0 g, 19 mmol) in THF (10 mL). After stirring 72 h, the solution was filtered and the solids washed with ether. The concentrated residue was taken up in ether, washed (2 M HCl, aq NaHC03, brine), dried (0259) (Na2S04), and concentrated. The resulting residue was subjected to chromatography on silica gel using a gradient up to 5% isopropanol in CH2CI2 to afford 4.5 g (71%) of the desired Boc-protected intermediate (B2).

Reference： [1]Patent: WO2018/53222,2018,A1 .Location in patent: Paragraph 00156
[2]Journal of Medicinal Chemistry,2018,vol. 61,p. 7525 - 7545

61
[ 2026-48-4 ]
[ 214630-00-9 ]
tert-butyl (3R)-7-hydroxy-3-[(2S)-1-hydroxy-3-methylbutan-2-yl]carbamoyl}-1,2,3,4-tetrahydroisoquinoline-2-carboxylate hydrochloride [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 7525 - 7545

62
[ 2026-48-4 ]
[ 17191-43-4 ]
[ 944281-99-6 ]

Reference： [1]Patent: EP1975162,2008,A1

63
[ 2026-48-4 ]
[ 140-89-6 ]
[ 76186-04-4 ]

Yield	Reaction Conditions	Operation in experiment
96%	In ethanol; at 100℃; for 24h;Inert atmosphere; Sealed tube;	General procedure: To the mixture of vicinal amino alcohol (1, 1.0 mmol, 1.0 equiv.) in absolute ethanol (2.0 mmol),potassium ethylxanthate (5.0 mmol, 5.0 equiv.) was added quickly. After flushed with N2 for 5 mins,the suspension was sealed and heated in an oil bath at 100 C for 24 hr. The it was cooled down toroom temperature, the mixture was transferred to a 50 mL-round bottom flask, and evaporated underreduced pressure to remove alcohol. Then water (10 mL) was added to the slurry and extracted withethyl acetate (30 mL*3). Combined organic phase was washed with brine (30 mL) and dried overanhydrous Na2SO4. After concentration, the crude product was obtained. Then it was applied onsilica gel for flash chromatography to afford corresponding 1,3-thiazolidine-2-thione (2). For somecases, 1,3-oxazolidine-2-thione (3) was obtained as side product.

Reference： [1]Synlett,2019,vol. 30,p. 713 - 716

64
[ 1070-34-4 ]
[ 2026-48-4 ]
ethyl (S)-3-(4-isopropyl-4,5-dihydrooxazol-2-yl)propanoate [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 2070 - 2073

65
[ 1070-34-4 ]
[ 2026-48-4 ]
ethyl 3-((2R,4S)-4-isopropyl-3-phenyl-2-(trichloromethyl)oxazolidin-2-yl)propanoate [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 2070 - 2073

66
[ 2026-48-4 ]
[ 1119-46-6 ]
2-(4-chlorobutyl)-4-isopropyl-3-phenyl-2-(trichloromethyl)oxazolidine [ No CAS ]
(2R,4S)-2-(4-chlorobutyl)-4-isopropyl-3-phenyl-2-(trichloromethyl)oxazolidine [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 2070 - 2073

67
[ 2026-48-4 ]
[ 1119-46-6 ]
(S)-2-(4-chlorobutyl)-4-isopropyl-4,5-dihydrooxazole [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 2070 - 2073

68
[ 6624-49-3 ]
[ 2026-48-4 ]
C₁₅H₁₈N₂O₂ [ No CAS ]

Reference： [1]Chemical Communications,2019,vol. 55,p. 5902 - 5905

69
[ 2026-48-4 ]
[ 106-49-0 ]
[ 4392-87-4 ]
(S)-6-(4-isopropyl-1-(p-tolyl)-4,5-dihydro-1H-imidazol-2-yl)-2,2′-bipyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
50%		(1) Preparation of (S)-6-(4-isopropyl-1-(p-tolyl)-4,5-dihydro-1H-imidazol-2-yl)-2,2'-bipyridine:2,2-bipyridyl-6-carboxylic acid (10 mmol)In thionyl chloride solution (5 mL)Reflow reaction for 8 h,The excess thionyl chloride was removed by rotary evaporation to give a pale yellow oil.Dissolve it in an anhydrous dichloromethane solution,In ice bath conditions,Adding and dissolving L-prolinol (11 mmol, 1.13 g) andTriethylamine (30mmol, 4.2 mL)In the anhydrous dichloromethane solution, after completion of the dropwise addition, the reaction was allowed to proceed at room temperature overnight.After completion of the reaction, the reaction was spun dry, ethyl acetate was added, and the insoluble material was removed by filtration.After the filtrate was spun dry, continue to add thionyl chloride (5 mL)Reacted under reflux for 8 h,The excess thionyl chloride was removed by rotary evaporation to give a reddish brown oil.Dissolve it in an anhydrous dichloromethane solution,In an ice bath, the solution was dissolved in p-toluidine (11 mmol, 1.2 g).And triethylamine (60 mmol, 8 mL)In anhydrous dichloromethane solution,After stirring at room temperature overnight,Add 10% aqueous sodium hydroxide solution (35 mL),Stirring was continued for 8-12 h at room temperature. After completion, the mixture was separated and the aqueous phase was extracted with dichloromethane three times.Drying with anhydrous magnesium sulfate, suction filtration, spin-drying and column chromatography (eluent ratio PE/EA = 3/1 to 1/10) gave the corresponding NNN' ligand.Brown solid; yield: 50%;

Reference： [1]Patent: CN109970814,2019,A .Location in patent: Paragraph 0018

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Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
P244	Keep reduction valves free from grease and oil.
P250	Do not subject to grinding/shock/friction.
P251	Pressurized container: Do not pierce or burn, even after use.
P260	Do not breathe dust/fume/gas/mist/vapours/spray.
P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
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. 2026-48-4 ]

Quality Control of [ 2026-48-4 ]

Related Doc. of [ 2026-48-4 ]

Product Details of [ 2026-48-4 ]

Calculated chemistry of [ 2026-48-4 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 2026-48-4 ]

Application In Synthesis of [ 2026-48-4 ]

[ 2026-48-4 ] Synthesis Path-Upstream 1~6

[ 2026-48-4 ] Synthesis Path-Downstream 1~69

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry