Trifluoroacetic acid → (3'R,4'R)-[1,3'-Bipyrrolidin]-4'-ol

Participants

Reaction Conditions

Reaction Steps

Dissolve 4′-hydroxy-[1,3′]bipyrrolidinyl-1′-carboxylic acid tert-butyl ester (751 mg, 2.93 mmol) in dichloromethane (13 mL) and cool the mixture to 0° C. Add trifluoroacetic acid (2.5 mL, 33.1 mmol) and warm the mixture to room temperature for one hour. Remove the volatiles via reduced pressure and then purify by applying to two 10 g SCX cartridges. Wash the material with methanol then elute the material with 2N ammonia in methanol to give 460 mg (99%) of the title compound as a clear oil. 1H NMR(DMSO-d6) δ 1.60 (m, 4H), 2.31 (s, 1H), 2.41 (m, 5H), 2.53 (m, 1H), 2.81 (m, 1H), 2.93 (m, 1H), 3.94 (s, 1H).

Provenance & Evidence