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Acetone → (S)-1-{4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-2-isopropylamino-4-methyl-pentan-1-one

HRID 2299893
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HRID 2299893 반응식
[NH2:1][C@@H:2]([CH2:31][CH:32]([CH3:34])[CH3:33])[C:3]([N:5]1[CH2:10][CH2:9][CH:8]([N:11]([C:17]2[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[CH:19][CH:18]=2)[CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH2:7][CH2:6]1)=[O:4].[CH3:35][C:36]([CH3:38])=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>C(Cl)Cl.CCOC(C)=O>[CH2:24]([O:23][C:20]1[CH:19]=[CH:18][C:17]([N:11]([CH2:12][CH:13]=[C:14]([CH3:16])[CH3:15])[CH:8]2[CH2:9][CH2:10][N:5]([C:3](=[O:4])[C@@H:2]([NH:1][CH:36]([CH3:38])[CH3:35])[CH2:31][CH:32]([CH3:34])[CH3:33])[CH2:6][CH2:7]2)=[CH:22][CH:21]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 180AcetoneHCID 5049666Sodium triacetoxyborohydrideHCID 10004622(S)-2-Amino-1-{4-[(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-4-methyl-pentan-1-one

생성물 1

HCID 10696911(S)-1-{4-[(4-Benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-2-isopropylamino-4-methyl-pentan-1-one수율 81%

시약·촉매·용매 2

HCID 6344
Dichloromethane
용매
HCID 8857Ethyl Acetate용매

실험 절차

A solution of (S)-2-Amino-1-{4-[(4-benzyloxy-phenyl)-(3-methyl-but-2-enyl)-amino]-piperidin-1-yl}-4-methyl-pentan-1-one (Example 20) (0.20 g, 0.43 mmol) and acetone (25 mg, 0.43 mmol) in CH2Cl2 (4 mL) was cooled to 0° C., treated with NaBH(OAc)3, allowed to warm to room temperature as ice melted and stir overnight. The reaction was diluted with EtOAc (100 mL), washed with saturated sodium bicarbonate solution and brine, dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel eluting with 5% MeOH/CH2Cl2 to give 176 mg (81%) of the desired product.

후처리

  1. washwashed with saturated sodium bicarbonate solution and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated
  4. customThe residue was chromatographed on silica gel eluting with 5% MeOH/CH2Cl2

출처 및 근거

ORD 기록
ord-fbad4d4e4a6f418b9c8da1e40255f63f
출처 데이터셋
uspto-grants-2002_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06495715B2

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