1,1'-Carbonyldiimidazole → HCID 67312124, compound

Participants

Reaction Steps

(3R,4S)-4-Amino-1-benzylpyrrolidin-3-ol (6 g, 31.4 mmol) in DMF (100 mL) was treated with CDI (5 g, 31.4 mmol) and the reaction mixture was stirred at r.t. for 18 h. The reaction was concentrated in vacuo and azeotroped with heptane. The residual oil was chromatographed on silica with a mixture of dichloromethane and methanol (gradient elution 0-10% methanol), yielding a colourless oil (6 g) which crystallized on standing. δH (DMSO-d6) 7.58 (1H, s), 7.29 (5H, m), 4.96 (1H, dd, J 7.9, 4.5 Hz), 4.16 (1H, dd, J 7.7, 4.9 Hz), 3.59 (2H, m), 3.00 (1H, d, J 11.1 Hz), 2.76 (1H, m), 2.19 (1H, dd, J 11.3, 4.5 Hz), 2.08 (1H, dd, J 10.2, 4.9 Hz).

Provenance & Evidence