Methanol → Trans-4-(4-bromo-benzyloxy)-L-proline Methyl Ester

Participants

Reaction Conditions

Reaction Steps

SOCl2 (0.27) was carefully added dropwise to 2.7 mL of MeOH at −5° C. To this mixture was added trans-N-Boc-4-(4-bromo-benzyloxy)-L-proline (0.25 g) in 2.7 mL of MeOH. The reaction mixture was allowed to warm to 20° C. and stirred overnight. The solvent was evaporated under reduced pressure and the residue dissolved in DCM. The organic layer was washed with water, dried over MgSO4, and evaporated in vacuo to afford the above-titled compound (60 mg). NMR (CDCl3, 200 MHz): 7.45 (2H, d), 7.2 (2H, d), 4.44 (2H, s), 4.15-4.05 (1H, m), 4.0 (1H, t), 3.7 (3H, s), 3.2-3.05 (2H,m), 2.27 (1H, dd), 2.05-1.9 (1H, m).

Provenance & Evidence