Aluminium lithium hydride → 2-Butyl-2-hydroxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
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
Product 1
Reagents, catalysts & solvents 1
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.