Sodium borohydride → HCID 66783140, compound

HRID 1096260Notes

Reaction equation

HRID 1096260 reaction equation
[BH4-].[Na+].C[O:4][C:5](=O)[CH:6]([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=2)[CH:29]([CH3:43])[C:28]1=[O:44])[CH2:7][CH2:8][O:9][Si:10]([C:23]([CH3:26])([CH3:25])[CH3:24])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>CCO>[C:23]([Si:10]([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[O:9][CH2:8][CH2:7][CH:6]([N:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:41])([F:40])[F:42])[CH:34]=2)[CH:29]([CH3:43])[C:28]1=[O:44])[CH2:5][OH:4])([CH3:24])([CH3:25])[CH3:26]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66783161HCID 66783161, compound

Product 1

HCID 66783140HCID 66783140, compoundYield 49.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (59 mg, 1.6 mmol) was added at RT to a solution of 4-(tert-butyl-diphenyl-silanyloxy)-2-[3-methyl-2-oxo-4-(3-trifluoromethyl-phenyl)-piperazin-1-yl]-butyric acid methyl ester (480 mg, 0.78 mmol) in EtOH (7 mL), then after 20 h the reaction mixture was partitioned between 10% aq. KHSO4 solution and CH2Cl2. The organic layer was dried (MgSO4), filtered, and evaporated. Chromatography (SiO2; heptane/EtOAc 4:1) afforded the title compound (224 mg, 49%). Light yellow oil, MS: 585.4 (M+H)+.

Workup

  1. customafter 20 h the reaction mixture was partitioned between 10% aq. KHSO4 solution and CH2Cl2
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated

Sources & evidence

ORD record
ord-09722c1f69b84654b022b7903e014c79
Source dataset
uspto-grants-2012_03
Patent number
US08138175B2

Reaction notes

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