Sodium borohydride → cis-3-Azido-2-hydroxymethyl-4-oxoazetidine

HRID 2050390Notes

Reaction equation

HRID 2050390 reaction equation
[N:1]([C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[C:9](OC)=[O:10])=[N+:2]=[N-:3].[BH4-].[Na+]>>[N:1]([C@H:4]1[C:7](=[O:8])[NH:6][C@H:5]1[CH2:9][OH:10])=[N+:2]=[N-:3]

Participants

3

Reactant 2

HCID 4311764Sodium borohydrideHCID 13566680Methyl (2R,3R)-3-azido-4-oxoazetidine-2-carboxylate

Product 1

HCID 86734333cis-3-Azido-2-hydroxymethyl-4-oxoazetidine

Procedure

Methyl cis-3-azido-4-oxoazetidine-2-carboxylate was reduced with sodium borohydride as described in Preparation 3 and the product was chromatographed on silica gel with ethyl acetate as eluant to give cis-3-azido-2-hydroxymethyl-4-oxoazetidine.

Workup

  1. customas described in Preparation 3
  2. customthe product was chromatographed on silica gel with ethyl acetate as eluant

Sources & evidence

ORD record
ord-15e7d169cddd4bb89cca48e45f836b69
Source dataset
uspto-grants-1980_04
Patent number
US04200572

Reaction notes

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