Sodium borohydride → HCID 86744035, compound

HRID 2107851Notes

Reaction equation

HRID 2107851 reaction equation
[CH:1]([C:3]1[NH:4][C:5]([CH3:34])=[C:6]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2/[CH:20]=[CH:21]/[C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])=[O:2].[BH4-].[Na+]>C(O)C>[OH:2][CH2:1][C:3]1[NH:4][C:5]([CH3:34])=[C:6]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2/[CH:20]=[CH:21]/[C:22]([O:24][C:25]([CH3:26])([CH3:27])[CH3:28])=[O:23])[C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86744036HCID 86744036, compound

Product 1

HCID 86744035HCID 86744035, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the product of Example 2 (0.95 g) in ethanol (20 ml) was treated at 0° with sodium borohydride (0.76 g). The mixture was stirred for 30 min. and extracted with ethyl acetate. After evaporation of the solvent the residue was purified by column chromatography on silica gel eluting with cyclohexane/ethyl acetate 1:1 to give the title compound (0.2 g) as a white solid. M.p. 163°-164°. T.l.c. (cyclohexane/ethyl acetate 1:1) Rf 0.23.

Workup

  1. extractionextracted with ethyl acetate
  2. customAfter evaporation of the solvent the residue
  3. customwas purified by column chromatography on silica gel eluting with cyclohexane/ethyl acetate 1:1

Sources & evidence

ORD record
ord-60c04c5cbb8c4800af732d860421a2c7
Source dataset
uspto-grants-1990_06
Patent number
US04935548

Reaction notes

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