Trifluoroacetic acid → (4S)-4-(Benzyloxy)-L-proline
Reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)[CH2:10][C@H:9]1[C:21]([OH:23])=[O:22])=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[CH2:14]([O:13][C@@H:11]1[CH2:12][NH:8][C@H:9]([C:21]([OH:23])=[O:22])[CH2:10]1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
(2S,4S)-1-(tert-butoxycarbonyl)-4-(benzyloxy)-pyrrolidine-2-carboxylic acid (Preparation 17, 150 mg, 0.47 mmol) was dissolved in dichloromethane (5 ml). Trifluoroacetic acid (5 ml) was added and the mixture left stirring overnight at room temperature. The reaction mixture was partitioned between dichloromethane (25 ml) and water (25 ml). The aqueous layer was separated, washed with more dichloromethane (25 ml) and evaporated to dryness. The product was purified using an ion exchange column (Dowex 50WX8-200 resin), eluting first with water then 9:1 water:ammonia yielding the title compound (34 mg, 33% yield) as a white solid.