Sodium borohydride → N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-3-hydroxy-1-(1-hydroxyethyl)cyclopentanecarboxamide

HRID 643544Notes

Reaction equation

HRID 643544 reaction equation
[C:1]([O:5][C:6]1[CH:24]=[CH:23][C:22]([C:25]([F:28])([F:27])[F:26])=[CH:21][C:7]=1[CH2:8][NH:9][C:10]([C:12]1([CH:18]([OH:20])[CH3:19])[CH2:16][CH2:15][C:14](=[O:17])[CH2:13]1)=[O:11])([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CO>[C:1]([O:5][C:6]1[CH:24]=[CH:23][C:22]([C:25]([F:26])([F:27])[F:28])=[CH:21][C:7]=1[CH2:8][NH:9][C:10]([C:12]1([CH:18]([OH:20])[CH3:19])[CH2:16][CH2:15][CH:14]([OH:17])[CH2:13]1)=[O:11])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 59261003N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-1-(1-hydroxyethyl)-3-oxocyclopentanecarboxamide

Product 1

HCID 59261007N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-3-hydroxy-1-(1-hydroxyethyl)cyclopentanecarboxamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A cooled (0° C.) solution of N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-1-(1-hydroxyethyl)-3-oxocyclopentanecarboxamide (6.27 g, 15.6 mmol) in methanol was treated with sodium borohydride (591 mg, 15.6 mmol) and stirred for 20 min. The reaction mixture was concentrated and the residue was partitioned between DCM and water. The organic layer was washed with brine, dried over anhydrous MgSO4, filtered, and concentrated to give N-[2-tert-butoxy-5-(trifluoromethyl)benzyl]-3-hydroxy-1-(1-hydroxyethyl)cyclopentanecarboxamide as a mixture of 8 isomers.

Workup

  1. concentrationThe reaction mixture was concentrated
  2. customthe residue was partitioned between DCM and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5d65e2c95f71425b910e9e551fd1dc96
Source dataset
uspto-grants-2010_04
Patent number
US07700591B2

Reaction notes

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