Sodium borohydride → HCID 66918731, compound

HRID 1367461Notes

Reaction equation

HRID 1367461 reaction equation
[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][C:9](=[O:11])[CH2:8][C@H:7]1[C:12](=[O:19])[NH:13][C:14]1([C:17]#[N:18])[CH2:16][CH2:15]1)=[O:5])[CH3:2].[BH4-].[Na+]>C1COCC1>[CH2:1]([O:3][C:4]([C@@H:6]1[CH2:10][CH:9]([OH:11])[CH2:8][C@H:7]1[C:12](=[O:19])[NH:13][C:14]1([C:17]#[N:18])[CH2:16][CH2:15]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 66918396HCID 66918396, compound

Product 1

HCID 66918731HCID 66918731, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (1R,2R)-2-(1-cyano-cyclopropylcarbamoyl)-4-oxo-cyclopentanecarboxylic acid ethyl ester (0.38 mmol) in THF (2.0 ml) was added at −15° C. sodium borohydride (0.38 mmol) and stirring was continued for 4 h. The mixture was partitioned between 1N aqueous HCl and ethyl acetate, the organic layer was dried, evaporated and the residue chromatographed on silica using ethyl acetate to give (1R,2R)-2-(1-cyano-cyclopropylcarbamoyl)-4-hydroxy-cyclopentanecarboxylic acid ethyl ester as a 2:1 mixture of epimers as a colorless solid. MS: 267.0 (M+H)+.

Workup

  1. customThe mixture was partitioned between 1N aqueous HCl and ethyl acetate
  2. customthe organic layer was dried
  3. customevaporated
  4. customthe residue chromatographed on silica

Sources & evidence

ORD record
ord-e54ae8711ab24ffabb0319038fdc0411
Source dataset
uspto-grants-2011_02
Patent number
US07893099B2

Reaction notes

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