4-Hydroxy-4-phenylcyclohexan-1-one → N-(2-{[3-(Fluoromethyl)-1-(4-hydroxy-4-phenylcyclohexyl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

HRID 1016081Notes

Reaction equation

HRID 1016081 reaction equation
[OH:1][C:2]1([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][C:5](=O)[CH2:4][CH2:3]1.[F:15][CH2:16][C:17]1([NH:22][C:23](=[O:38])[CH2:24][NH:25][C:26](=[O:37])[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:35])[F:34])[CH:28]=2)[CH2:21][CH2:20][NH:19][CH2:18]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[F:15][CH2:16][C:17]1([NH:22][C:23](=[O:38])[CH2:24][NH:25][C:26](=[O:37])[C:27]2[CH:32]=[CH:31][CH:30]=[C:29]([C:33]([F:36])([F:34])[F:35])[CH:28]=2)[CH2:21][CH2:20][N:19]([CH:5]2[CH2:6][CH2:7][C:2]([OH:1])([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:3][CH2:4]2)[CH2:18]1

Participants

5

Reactant 3

HCID 5837414-Hydroxy-4-phenylcyclohexan-1-oneHCID 5049666Sodium triacetoxyborohydrideHCID 59556164N-(2-{[3-(fluoromethyl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide

Product 1

HCID 59556167N-(2-{[3-(Fluoromethyl)-1-(4-hydroxy-4-phenylcyclohexyl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamideYield 16.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

100 mg (0.53 mmol) of 4-hydroxy-4-phenylcyclohexanone and 184 mg (0.53 mmol) of N-(2-{[3-(fluoromethyl)pyrrolidin-3-yl]amino}-2-oxoethyl)-3-(trifluoromethyl)benzamide were dissolved in 10 mL of methylene chloride. To the solution was added 221 mg (1.06 mmol) of sodium triacetoxyborohydride. The reaction mixture was stirred at room temperature for 2 h. Direct chromatography on silica gel gave the final desired product 41 mg (top spot on TLC and first peak on HPLC, yield: 16.7%, MS: 522 (M+1)+) and the other isomer 51 mg (second peak on HPLC, yield: 20%, MS: 522 (M+1)+).

Sources & evidence

ORD record
ord-fc1a93ac62284f06a8a884c8a37069d5
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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