Sodium borohydride → HCID 67973476, compound

HRID 1184707Notes

Reaction equation

HRID 1184707 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16](=[O:35])[CH2:17][C:18]2[C:23]([Cl:24])=[CH:22][N:21]=[C:20]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=3)[N:19]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>O1CCCC1.O>[C:3]([O:7][C:8]([N:10]1[CH2:15][CH2:14][CH:13]([CH:16]([OH:35])[CH2:17][C:18]2[C:23]([Cl:24])=[CH:22][N:21]=[C:20]([C:25]3[CH:30]=[CH:29][C:28]([S:31]([CH3:34])(=[O:33])=[O:32])=[CH:27][CH:26]=3)[N:19]=2)[CH2:12][CH2:11]1)=[O:9])([CH3:5])([CH3:6])[CH3:4]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 67973502HCID 67973502, compound

Product 1

HCID 67973476HCID 67973476, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Sodium borohydride (50 mg) is added to an ice-cooled solution of 4-{2-[5-chloro-2-(4-methanesulfonyl-phenyl)-pyrimidin-4-yl]acetyl}-piperidine-1-carboxylic acid tert-butyl ester (280 mg) in a mixture of tetrahydrofuran (10 mL) and water (2 mL). The ice bath is removed after 5 min and the reaction mixture is stirred for 0.5 h at room temperature. 2 N Citric acid is added and the mixture is extracted with ethyl acetate. The combined extracts are washed with aqueous NaHCO3 solution and brine, dried over MgSO4, and concentrated in vacuo. The residue is chromatographed on silica gel (cyclohexane/ethyl acetate 40:60→0:100) to give the title compound. LC (method 7): tR=1.48 min; Mass spectrum (ESI−): m/z=494 [M−H]−.

Workup

  1. customThe ice bath is removed after 5 min
  2. addition2 N Citric acid is added
  3. extractionthe mixture is extracted with ethyl acetate
  4. washThe combined extracts are washed with aqueous NaHCO3 solution and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue is chromatographed on silica gel (cyclohexane/ethyl acetate 40:60→0:100)

Sources & evidence

ORD record
ord-7ab5e64094ac4f07803851d620db191d
Source dataset
uspto-grants-2014_03
Patent number
US08669271B2

Reaction notes

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