Methanol → HCID 23138996, compound

HRID 1171739Notes

Reaction equation

HRID 1171739 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]1[CH:15]=[CH:14][C:13](/[CH:16]=[C:17]2\[CH2:18][N:19]([C:24]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:20][CH2:21][C:22]\2=[O:23])=[N:12]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].ClCCl.CO.[BH4-].[Na+]>O>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][N:11]1[CH:15]=[CH:14][C:13](/[CH:16]=[C:17]2\[CH2:18][N:19]([C:24]([C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)[C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[CH2:20][CH2:21][CH:22]\2[OH:23])=[N:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 23138656HCID 23138656, compound

Product 1

HCID 23138996HCID 23138996, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of (E)-3-({1-[2-(t-butoxycarbonylamino)ethyl]-1H-pyrazol-3-yl}methylidene)-1-(triphenylmethyl)piperidin-4-one (6.41 g) in a mixed solvent of dichloromethane (40 ml) and methanol (40 ml) was added sodium borohydride (436 mg) at 0° C. After the resulting mixture was stirred at 0° C. for 30 minutes, water was added to the mixture to stop the reaction and the product was extracted with ethyl acetate. The organic layer was washed with water and saturated aqueous sodium chloride successively, and dried over anhydrous sodium sulfate. The solvent was removed in vacuo, and the residue was purified by chromatography on silica gel using a mixture of ethyl acetate and hexane (3:7 to 7:3) as eluents to afford the title compound as a colourless solid (5.35 g, yield: 84%)

Workup

  1. customthe reaction
  2. extractionthe product was extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated aqueous sodium chloride successively
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was removed in vacuo
  6. customthe residue was purified by chromatography on silica gel using
  7. additiona mixture of ethyl acetate and hexane (3:7 to 7:3) as eluents

Sources & evidence

ORD record
ord-6c89b6542e59409c8d574f323031ecea
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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