Water → HCID 67751591, compound

Participants

Reaction Steps

To a solution of cis-2-(diphenylmethyl)-3-(3,5-dimethylbenzyloxy)-1-ethoxycarbonylpyrrolidine (Example 1e, 0.500 g, 1.1 mmol) in tetrahydrofuran (5.0 ml) was added 1.0M lithium aluminium hydride (5.0 ml, 5.0 mmol) and then the solution heated at reflux for 1 h. To the cooled solution was carefully added water (2 ml), 4M sodium hydroxide (2 ml) and water (4 ml) followed by ethyl acetate. The suspension was filtered through Celite and the filtrate was washed with saturated brine and dried (MgSO4). Removal of the solvent in vacuo gave cis-2-(diphenylmethyl)-3-(3,5-dimethylbenzyloxy)-1-methylpyrrolidine, as an oil. 1H NMR (360 MHz, CDCl3) δ7.05-7.43 (10H, m), 6.85 (1H, s), 6.68 (2H, s), 4.30 (1H, d, J=15.0 Hz), 4.01 (1H, d, J=16.0 Hz), 3.77 (1H, m), 3.63 (1 H, d, J=16.0 Hz), 3.24 (2H, m), 2.30 (1H, m), 2.26 (6H, s), 1.91 (5H, m).

Provenance & Evidence