Phosphate → HCID 71226774, compound

Participants

Reaction Conditions

Reaction Steps

A solution of LiHMDS (1.0 M in THF, 0.908 ml, 0.980 mmol) was slowly added to a solution of (2S,5R)-methyl 1-benzyl-5-(3-methoxy-3-oxopropyl)pyrrolidine-2-carboxylate (126, mg, 0.413 mmol) in THF (4 ml) at −78° C. The reaction mixture was stir at −78° C. for 6 hrs. Then the reaction mixture was poured into a 0° C. stirring mixture of EtOAc (10 mL) and pH 7.0 aqueous phosphate buffer. The organic phase was separated, washed with saturated aqueous NaCl solution, dried over MgSO4, filtered and concentrated. The resulting residue was purified using silica gel chromatography (ISCO system) to give the product methyl 8-benzyl-2-hydroxy-8-azabicyclo[3.2.1]oct-2-ene-3-carboxylate (74 mg, 0.271 mmol) as a syrup. Anal. Calcd. for C16H19NO3 m/z 273.1, found: 274.1 (M+H)+; 1H NMR (400 MHz, CDCl3) δ ppm 7.40-7.21 (5 H, m), 3.80-3.73 (4 H, m), 3.70 (2 H, d, J=3.0 Hz), 3.36 (1 H, t, J=5.2 Hz), 3.32 (1 H, d, J=5.6 Hz), 2.63 (1 H, dd, J=15.9, 4.8 Hz), 2.18-2.11 (2 H, m), 2.02-1.95 (1 H, m), 1.85 (1 H, d, J=15.9 Hz), 1.59-1.48 (1 H, m).

Provenance & Evidence