Borane → (1-Benzylpyrrolidin-3-yl)methanol

Participants

Reaction Steps

Reduction of 1-benzyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester 11 with a suitable reducing agent (such as lithium aluminum hydride, borane, and the like) gives N-benzyl-3-hydroxymethylpyrrolidine 12. Removal of the benzyl group under catalytic hydrogenation reaction conditions followed by reaction of 3-hydroxymethylpyrrole 13 with di-tert-butyl dicarbonate in the presence of a base (e.g., sodium hydroxide, sodium carbonate, and the like) gives N-tert-butoxycarbonyl-3-hydroxymethylpyrrolidine of Formula (Ic). Compound (Ic) is then converted to a compound of Formula (I) as shown below.

Provenance & Evidence