Sodium → (3S)-3-(Cyclobutyl-hydroxy-methyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1922167Notes

Reaction equation

HRID 1922167 reaction equation
[Na].[C:2]([O:6][C:7]([N:9]1[CH2:13][CH2:12][C@H:11]([C:14]([CH:16]2[CH2:19][CH2:18][CH2:17]2)=[O:15])[CH2:10]1)=[O:8])([CH3:5])([CH3:4])[CH3:3]>CO>[C:2]([O:6][C:7]([N:9]1[CH2:13][CH2:12][C@H:11]([CH:14]([CH:16]2[CH2:17][CH2:18][CH2:19]2)[OH:15])[CH2:10]1)=[O:8])([CH3:5])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 5360545SodiumHCID 59536623HCID 59536623, compound

Product 1

HCID 59536654(3S)-3-(Cyclobutyl-hydroxy-methyl)-pyrrolidine-1-carboxylic acid tert-butyl esterYield 82.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Add sodium borohyride (1.19 g, 31.4 mmol) to a stirred solution of (S)-3-cyclobutanecarbonyl-pyrrolidine-1-carboxylic acid tert-butyl ester (5.30 g, 20.9 mmol) in MeOH (105 mL) kept under an atmosphere of nitrogen at 0° C. Stir the mixture for 2 hours while warming to room temperature. Concentrate the MeOH, dilute with dichloromethane and wash the organics with saturated aqueous NaHCO3, water and brine. Dry (MgSO4), filter and concentrate under reduced pressure to yield the title compound (4.4 g, 82%) as a mixture of diastereomers (S-mix).

Workup

  1. customkept under an atmosphere of nitrogen at 0° C
  2. concentrationConcentrate the MeOH
  3. additiondilute with dichloromethane
  4. washwash the organics with saturated aqueous NaHCO3, water and brine
  5. dry with materialDry (MgSO4)
  6. filtrationfilter
  7. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-6465767145d3495ca8dff35cedb289b9
Source dataset
uspto-grants-2012_05
Patent number
US08173821B2

Reaction notes

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