Sodium borohydride → HCID 57248109, compound

HRID 617378Notes

Reaction equation

HRID 617378 reaction equation
C([C@H]1[O:9][C:8](=[O:10])[C@@:7]([C@H:17]2[CH2:21][CH2:20][C:19](=[O:22])[CH2:18]2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6]1)(C)(C)C.[BH4-].[Na+]>CO.C(OCC)C>[OH:22][CH:19]1[CH2:20][CH2:21][C@H:17]([C@@:7]([OH:6])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8]([OH:10])=[O:9])[CH2:18]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 54308542(2R,5R)-2-(t-butyl)-5-[(1S)-3-oxocyclopentyl]-5-phenyl-1,3-dioxolan-4-one

Product 1

HCID 57248109HCID 57248109, compoundYield 118.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 169 mg of (2R,5R)-2-(t-butyl)-5-[(1S)-3-oxocyclopentyl]-5-phenyl-1,3-dioxolan-4-one in 2 ml of methanol, 71 mg of sodium borohydride was added under cooling with ice, followed by stirring for 30 minutes at the same temperature. The reaction mixture was diluted with diethyl ether, washed with water and then brine, and dried over anhydrous magnesium sulfate. Distilling the solvent off under reduced pressure, 157 mg of the title compound was obtained as a colorless oil.

Workup

  1. temperatureunder cooling with ice
  2. washwashed with water
  3. dry with materialbrine, and dried over anhydrous magnesium sulfate
  4. distillationDistilling the solvent off under reduced pressure

Sources & evidence

ORD record
ord-6276091f353e49d5a94a1b585ea7c852
Source dataset
uspto-grants-1999_09
Patent number
US05948792

Reaction notes

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