Sodium borohydride → HCID 59536646, compound

HRID 1922166Notes

Reaction equation

HRID 1922166 reaction equation
[BH4-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH2:14][CH2:13][C@H:12]([C:15](=[O:19])[CH2:16][CH2:17][CH3:18])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]>CO>[C:3]([O:7][C:8]([N:10]1[CH2:14][CH2:13][C@H:12]([CH:15]([OH:19])[CH2:16][CH2:17][CH3:18])[CH2:11]1)=[O:9])([CH3:6])([CH3:5])[CH3:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 59536640HCID 59536640, compound

Product 1

HCID 59536646HCID 59536646, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium borohydride (5.19 g, 145 mmol) portion wise to a solution of (S)-3-butanoyl-pyrrolidine-1-carboxylic acid tert-butyl ester (7.0 g, 29.0 mmol) in methanol (200 mL) and stir at room temperature over night. Add more sodium borohydride (1.4 g, 39 mmol) and stir an hour at room temperature. Evaporate the methanol to half volume, add brine and extract with ethyl acetate. Dry the combine organic phases (MgSO4), filter and concentrate under reduced pressure. Separate the diastereoisomers by silica gel chromatography eluting with 5% isopropylamine in hexanes to provide (3S)-3-(1-hydroxy-butyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, isomer 1 (S-1) as the first eluting isomer (2.6 g, 37%) and (3S)-3-(1-hydroxy-butyl)-pyrrolidine-1-carboxylic acid tert-butyl ester, isomer 2 (S-2) as the second eluting isomer (1.8 g, 26%)

Workup

  1. stirringstir an hour at room temperature
  2. customEvaporate the methanol to half volume
  3. additionadd brine
  4. extractionextract with ethyl acetate
  5. dry with materialDry the combine organic phases (MgSO4)
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure
  8. customSeparate the diastereoisomers by silica gel chromatography
  9. washeluting with 5% isopropylamine in hexanes

Sources & evidence

ORD record
ord-8da5581e1235407eb3a2edf0b0e269bf
Source dataset
uspto-grants-2012_05
Patent number
US08173821B2

Reaction notes

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