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

HRID 1069449Notes

Reaction equation

HRID 1069449 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-b869030a7b774156a12e908944cff15f
Source dataset
uspto-grants-2001_06
Patent number
US06251918B1

Reaction notes

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