Diethyl Ether → (cis-1-Benzylpyrrolidine-3,4-diyl)dimethanol

Participants

Reaction Conditions

Reaction Steps

Dimethyl (cis)-1-(phenylmethyl)-3,4-pyrrolidinedicarboxylate (Chem. Pharm. Bull. 1985 33; 896-898) (2.44 g, 8.8 mmol) was dissolved in THF (100 mL) and cooled to 0° C. LiAlH4 (1 g, 26 mmol) was added in portions and the reaction was heated overnight at 60° C. Upon cooling to 0° C., wet ether was added followed by water (1 mL), 15 w/w NaOH (aq) (1 mL) and water (3 mL). The resulting mixture was stirred for 15 min and filtered through Celite yielding crude [(cis)-1-(phenylmethyl)-3,4-pyrrolidinediyl]dimethanol (2.5 g) which was used directly in the next reaction. LCMS: (M+H)+: 222.3.

Provenance & Evidence