Aluminium lithium hydride → 2-Butyl-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

HRID 1894989Notes

Reaction equation

HRID 1894989 reaction equation
C[O:2][C:3]([C:5]1([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:9][CH2:8][CH2:7][N:6]1[C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])=O.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[C:13]([O:12][C:10]([N:6]1[CH2:7][CH2:8][CH2:9][C:5]1([CH2:17][CH2:18][CH2:19][CH3:20])[CH2:3][OH:2])=[O:11])([CH3:16])([CH3:15])[CH3:14]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 666872182-Butyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

Product 1

HCID 666873392-Butyl-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl esterYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of 2-butyl-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (0.842 g, 2.95 mmol) in THF (30 mL) at 0° C. under nitrogen was added LiAlH4 (2.95 mL of a 1.0 M solution in THF, 2.95 mmol) dropwise. After 15 min the reaction mixture was quenched by the addition of sodium sulfate decahydrate (2.5 g) then filtered. The filter cake was washed with DCM (50 mL) then the combined filtrates were concentrated in vacuo to give 2-butyl-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester (0.763 g) as a clear, colourless oil that was used directly without further purification.

Workup

  1. customAfter 15 min the reaction mixture was quenched by the addition of sodium sulfate decahydrate (2.5 g)
  2. filtrationthen filtered
  3. washThe filter cake was washed with DCM (50 mL)
  4. concentrationthe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-01f4df68998349e9bfa7231aeee392c6
Source dataset
uspto-grants-2013_08
Patent number
US08513425B2

Reaction notes

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