Methyl 1-benzyl-4-phenylpyrrolidine-3-carboxylate → 1-Benzyl-4-phenyl-3-pyrrolidinemethanol

Participants

Reaction Conditions

Reaction Steps

A solution of 2.61 g (8.8 mmol) of 1-phenylmethyl-3-(SR)-carbomethoxy-4-(SR)-phenylpyrrolidine (from Example 1, Step A) in 100 mL of THF at -78 ° C. was treated with 9.2 mL of 1.5 M diisobutyl-aluminum hydride solution in toluene. The reaction was warmed to 0 ° C. and stirred for 1 h. The reaction was quenched with 50 mL of sat'd sodium potassium tartrate solution, diluted with 100 mL of ether and stirred at rt for 20 h. The layers were separated and the organic layer was washed with 75 mL of H2O, dried over MgSO4 and concentrated in vacuo. Flash chromatography on 100 g of silica gel using 1:1 v/v, then 3:2 v/v EtOAc/hexanes as the eluant afforded 1.99 g (84%) of the title compound as a solid. 1H NMR (500 MHz, CDCl3): δ2.56-2.63 (m, 1H), 2.80 (dd, J=4.3, 9.4, 1H), 2.91-2.98 (m, 2H), 3.05 (dd, J=6.9, 9.6, 1H), 3.27 (dd, J=5.0, 10.7, 1H), 3.44 (dd, J=5.5, 10.8, 1H), 3.62 (q, J=9.0, 1H), 3.76 (ABq, J=24.2, 2H), 7.22-7.40 (10H). Mass Spectrum (NH3 -CI): m/z 268 (M+1).

Provenance & Evidence