3-(r)-t-Butyldimethylsilyloxymethyl-4-(s)-(3-fluorophenyl)pyrrolidine → 2-(r)-(3-(r)-(t-Butyldimethylsilyloxymethyl)-4-(s)-(3-fluoro-phenyl)pyrrolidin-1-yl)-3-(cyclopropyl)propanoic acid, 4-(methoxy)benzyl ester

Participants

Reaction Steps

The title compound was prepared from 200 mg (0.8 mmol) of 2-(S)-hydroxy-3-cyclopropyl propanoic acid, 4-(methoxy)benzyl ester (from EXAMPLE 21, Step B) and 321 mg (1.0 mmol) of 3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-(3-fluorophenyl)pyrrolidine (from EXAMPLE 20, Step H) using a procedure analogous to that described in EXAMPLE 1, Step G to provide 396 mg (91%) of the title compound: RF: 0.59 (4:1 a/v hexanes/EtOAc); 1H NMR (300 MHz) δ 0.01-0.14 (m, 81), 0.39-0.54 (m, 2H), 0.72 (m, 11H), 0-85 (s, 9H), 1.61-1.72 (m, 2H), 2.34 (m, 1H), 2.64 (br t, 1H), 2.75 (br t, 1H), 2.95-3.17 (m, 31), 3.38-3.60 (m, 3H), 3.82 (s, 3H), 5.13 (s, 3H), 6.85-7.00 (m, 5H), 7.18-7.36 (m, 3H).

Provenance & Evidence