Methyl bromoacetate → (3-(R)-t-Butyldimethylsilyloxymethyl-4-(S)-(3-fluorophenyl)pyrrolidin-1-yl)-acetic Acid, Methyl Ester

Participants

Reaction Conditions

Reaction Steps

A solution of 1.0 g (3.23 mmol) of (3-(R)-t-Butyldimethylsilyloxymethyl-4-(S)-(3-fluorophenyl)pyrrolidine in 8 mL of acetonitrile was treated with 0.47 mL (4.95 mmol) of methyl bromoacetate and 0.86 g (4.95 mmol) of DIEA and the reaction was heated in 80° C. bath. After 2 hr, the solution was cooled, and partitioned between water-EtOAc. The organic layer was washed with brine, dried and concentrated. The residue was purified on a flash column using a gradient of 10-20% EtOAc in hexanes to isolate 0.45 g of the title compound. 1H NMR (CDCl3) 0.027 (2s, 6H), 0.87 (s, 9H), 2.4 (m, 1H), 2.7-3.1 (m, 5H), 3.33 and 3.47 (ABq, 2H), 3.63 (m, 2H), 3.76 (s, 3H), 6.8-7.3 (m 4H).

Provenance & Evidence