3,5-Dimethylbenzyl bromide → HCID 67751544, compound

Participants

Reaction Steps

To a solution of cis-2-(diphenylmethyl)-3-hydroxy-1-ethoxycarbonylpyrrolidine (Example 1d, 1.00 g, 3.1 mmol) in ethylene glycol dimethyl ether (10.0 ml) was added 0.5M potassium bis(trimethylsilyl)amide (9.00 ml, 4.5 mmol) and stirred at room temperature for 1/2h before addition of 3,5dimethylbenzyl bromide (0.92 g, 4.5 mmol) in ethylene glycol dimethyl ether (2 ml). After stirring for 18 h the solvent was removed in vacuo and the residue partitioned between water/dichloromethane. The organic phase was washed with saturated brine and dried (MgSO4). The residue, after removal of solvent in vacuo, was chromatographed on silica gel using ethyl acetate/hexane (2:3) as eluant to give cis-2-(diphenylmethyl)-3-(3,5-dimethylbenzyloxy)-1-ethoxycarbonylpyrrolidine. 1H NMR (360 MHz, DMSO-d6) δ7.05-7.46 (10H, m), 6.81 (1H, s), 6.58 (2H, s), 4.86 (1H, t, J=7.0 Hz), 4.42 (1H, d, 7.5 Hz), 4.18 (1H, d, J=12.0 Hz), 4.11 (1H, m), 3.97 (1H, d, J=12.0 Hz), 3.83 (1H, m), 3.68 (1H, m), 3.31 (1H, m), 2.98 (1H, m), 2.19 (6H, s), 2.15 (1H, m), 1.95 (1H, m), 1.03 (3H, t, J=7.0 Hz). m/z (CI+) 444 (MH).

Provenance & Evidence