(3R,4S)-3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-phenylpyrrolidine → HCID 131722798, compound

Participants

Reaction Steps

The title compound was prepared from 233 mg (0.88 mol) of (R/S)-2-hydroxy-cyclopentylacetic acid, 4-(methoxy)benzyl ester (from EXAMPLE 15, Step B) and 209 mg (0.71 mmol) of 3-(R)-(t-butyldimethylsilyloxymethyl)-4-(S)-phenylpyrrolidine (from EXAMPLE 1, Step E) using a procedure analogous to that described in EXAMPLE 1, Step G to provide 326 mg (84%) of the title compounds as a mixture of diastereomers: RF: 0.64 (4:1 v/v hexanes/EtOAc); 1H NMR (300 Hz) δ 0.0 (2 s, 6H), 0.84, 0.85 (2 s, 9H), 1.18 (m, 11H), 1.42-1.82 (m, 7H), 2.23-2.34 (m, 2H), 2.65-3.18 (m, 6H), 3.43-3.59 (m, 2H), 3.81 (s, 3H), 5.01-5.19 (m, 2H), 6.85-6.91 (m, 2H), 7.14-7.36 (m, 7H).

Provenance & Evidence