Diisopropylethylamine → 4-[[(7aS)-2-(2-bromophenyl)-hexahydro-1-oxo-3H-pyrrolo[1,2-c]imidazol-3-ylidene]amino]-3-hydroxybenzonitrile

Participants

Reaction Steps

The standard procedure was followed using N-(4-cyano-2-t-butyldimethylsilanoxyphenyl)-N′-(2-bromophenyl)carbodiimide (54 mg, 0.13 mmol), diisopropylethylamine (32 μL, 0.29 mmol), L-proline benzylester hydro chloride (34 mg, 0.14 mmol) and TBAF (0.16 mL, 0.16 mmol) in THF (2 mL) and methanol (0.1 mL) to give 36 mg (67%) of 4-[[(7aS)-2-(2-bromophenyl)-hexahydro-1-oxo-3H-pyrrolo[1,2-c]imidazol-3-ylidene]amino]-3-hydroxybenzonitrile as a tan powder. 1H NMR (400 MHz, MeOD) δ 7.6 (2H, m), 7.35 (3H, m), 7.15 (1H, m), 7.0 (1H, m), 4.5 (1H, t), 3.0 (1H, m), 2.4 (1H, m), 2.2 (1H, m), 2.05 (2H, m); MS(EI) m/e 412 (M+).

Provenance & Evidence