Sodium borohydride → (3S,4S)-tert-Butyl 3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate

HRID 401874Notes

Reaction equation

HRID 401874 reaction equation
C([O:3][C:4]([C@H:6]1[C@H:10]([C:11](OCC)=[O:12])[CH2:9][N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:7]1)=O)C.[BH4-].[Na+]>C1COCC1.CO>[C:19]([O:18][C:16]([N:8]1[CH2:7][C@@H:6]([CH2:4][OH:3])[C@H:10]([CH2:11][OH:12])[CH2:9]1)=[O:17])([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 59512444(3R,4R)-1-tert-butyl 3,4-diethyl pyrrolidine-1,3,4-tricarboxylate

Product 1

HCID 59512458(3S,4S)-tert-Butyl 3,4-bis(hydroxymethyl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of (±)-trans-pyrrolidine-1,3,4-tricarboxylic acid 1-tert-butyl ester 3,4-diethyl ester (15.85 mmol, 5 g) in a mixture of THF (50 mL) and methanol (50 mL) was added NaBH4 (4 g) portions wise over a period of 1 h. The volatiles were removed under reduced pressure. To the residue was added water and extracted with DCM. The organic layer was dried and concentrated under reduced pressure. The residue was purified by flash silica gel column chromatography by eluting with ethyl acetate to provide (±)-trans-3,4-bis-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester.

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionTo the residue was added water
  3. extractionextracted with DCM
  4. customThe organic layer was dried
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash silica gel column chromatography
  7. washby eluting with ethyl acetate

Sources & evidence

ORD record
ord-237836f6190240f0bbf6090fd171ed8c
Source dataset
uspto-grants-2014_06
Patent number
US08741900B2

Reaction notes

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