Water → HCID 67547185, compound

Participants

Reaction Steps

To a solution of 4-azido-1-benzyl-pyrrolidine-2-carboxylic acid methyl ester (6 g, 23 mmol) in THF (100 ml) under N2 was added triphenylphosphine (12.08 g, 46 mmol) and water (1.036 mL, 57.56 mmol). The mixture was refluxed with stirring for 6 h. After removal of THF, the residue was dissolved in Et2O, treated with 0.15N aqueous HCl, stirred for 5 min, and extracted with Et2O (2×150 ml). The aqueous solution was then treated with 10% NaHCO3 until PH>10, and extracted by DCM (2×100 ml). The combined organic phases were dried over anhydrous NaSO4, concentrated to afford product 4-amino-1-benzyl-pyrrolidine-2-carboxylic acid methyl ester 4.6 g (85%) as colorless oil. MS m/e=235.3 [M+H]+.

Provenance & Evidence