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

HRID 2299893Notes

Reaction equation

HRID 2299893 reaction equation
[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

Participants

6

Reactant 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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-fbad4d4e4a6f418b9c8da1e40255f63f
Source dataset
uspto-grants-2002_12
Patent number
US06495715B2

Reaction notes

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