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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 1173290
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HRID 1173290 반응식
[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
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5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344
Dichloromethane
용매

실험 절차

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)+).

출처 및 근거

ORD 기록
ord-dfbf3c2c76a24db29377447ea4150c83
출처 데이터셋
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07834021B2

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