Sodium borohydride → HCID 54423437, compound

HRID 654878Notes

Reaction equation

HRID 654878 reaction equation
[C:1]([C@@H:9]1[O:13][C:12]([CH3:15])([CH3:14])[N:11]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C@H:10]1[CH2:23][CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+]>CO.C(O)(=O)C>[CH:24]1([CH2:23][C@H:10]2[C@H:9]([C@@H:1]([OH:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[O:13][C:12]([CH3:15])([CH3:14])[N:11]2[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 53845871HCID 53845871, compound

Product 1

HCID 54423437HCID 54423437, compoundYield 20.6%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 887MethanolSolvent

Procedure

290 mg (0.72 mmol) of t-butyl (4S,5R)-5-benzoyl-4-(cyclohexylmethyl)-2,2-dimethyl-3-oxazolidinecarboxylate in 5 ml of methanol are stirred at room temperature for 1 hour with 27 mg (0.7 mmol) of sodium borohydride. Thereafter, the reaction mixture is treated with two drops of glacial acetic acid and evaporated to dryness. The residue is chromatographed on 30 g of silica gel with a 4:1 mixture of hexane and ether as the eluting agent, with a methylene chloride solution of the crude product being applied to the column. In this manner there are obtained 60 mg of t-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(S)-α-hydroxybenzyl]-2,2-dimethyl-3-oxazolidinecarboxylate as a white solid, MS: 403 (M)+, as well as 210 mg of the epimeric t-butyl (4S,5R)-4-(cyclohexylmethyl)-5-[(R)-α-hydroxybenzyl]-2,2-dimethyl-3-oxazolidinecarboxylate also as a white solid, MS: 403 (M)+.

Workup

  1. customevaporated to dryness
  2. customThe residue is chromatographed on 30 g of silica gel with a 4:1 mixture of hexane and ether as the eluting agent, with a methylene chloride solution of the crude product

Sources & evidence

ORD record
ord-32317168fb9a4ad48e1d7dcbc1e3ed90
Source dataset
uspto-grants-1992_07
Patent number
US05134123

Reaction notes

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