Dichloromethane → HCID 23138491, compound

HRID 1171706Notes

Reaction equation

HRID 1171706 reaction equation
[BH4-].[Na+].[CH2:3]([O:5][C:6]([CH2:8][N:9]1[C:13](/[CH:14]=[C:15]2\[CH2:16][N:17]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH2:18][CH2:19][C:20]\2=[O:21])=[CH:12][N:11]=[CH:10]1)=[O:7])[CH3:4].ClCCl>C(O)C>[CH2:3]([O:5][C:6]([CH2:8][N:9]1[C:13](/[CH:14]=[C:15]2\[CH2:16][N:17]([C:22]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[CH2:18][CH2:19][CH:20]\2[OH:21])=[CH:12][N:11]=[CH:10]1)=[O:7])[CH3:4]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 23139177HCID 23139177, compound

Product 1

HCID 23138491HCID 23138491, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (0.06 g) was added to a solution of (E)-3-{[1-(ethoxycarbonylmethyl)-1H-imidazol-5-yl]methylidene}-1-(triphenylmethyl)piperidin-4-one (1.5 g) in a mixed solvent of dichloromethane (10 ml) and ethanol (10 ml) at 0° C. After the mixture was stirred at 0° C. for 0.5 hour and then at room temperature for 1.5 hour, it was partitioned between water and ethyl acetate. The organic layer was separated, washed with a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. Removal of the solvent under reduced pressure followed by purification of the residue by silica gel chromatography using dichloromethane and methanol (19:1) as an eluent to give the title compound (560 mg, yield: 37%) as a yellow amorphous solid.

Workup

  1. waitat room temperature for 1.5 hour
  2. customit was partitioned between water and ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with a saturated aqueous sodium chloride solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customRemoval of the solvent under reduced pressure
  7. customfollowed by purification of the residue by silica gel chromatography

Sources & evidence

ORD record
ord-0b5cedfe96d54ee7a9eea08de63a17da
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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