Tetrabutylammonium Fluoride → alpha-(R)-(3-(R)-(Hydroxymethyl)-4-(S)-(3-fluorophenyl)-pyrrolidin-1-yl)-isopropylacetic Acid, Para-methoxybenzyl Ester

Participants

Reaction Steps

The title compound was prepared from 14.84 g of α-(R)-(3-(S)-((tert-butyldimethylsilyloxy)methyl)-4-(S)-(3-fluorophenyl)-pyrrolidin-1-yl)-isopropylacetic acid, para-methoxybenzyl ester (from Step B above) and 125 mL of 1M solution of tetrabutylammonium fluoride in 125 mL of THF using a procedure analogous to that described in Example 1, Step B, Aldehyde 1. After purification with flash chromatography on silica gel, 10.75 g of the title compound was obtained as a colorless oil. RF: 0.23 (30% EtOAc in hexanes with 1% (v/v) Et3N). 1H NMR (500 MHz, CDCl3): δ7.33˜7.36 (m, 2H), 7.22˜7.26 (m, 1H), 6.88˜6.98 (m, 5H), 5.14 (AB d, 12.3 Hz, 1H), 5.13 (AB d, 12.3 Hz, 1H), 3.82 (s, 3H), 3.68 (dd, 4.6 & 10.6 Hz, 1H), 3.57 (dd, 6.1 & 10.5 Hz, 1H), 3.25˜3.29 (m, 1H), 3.05˜3.16 (m, 3H), 2.73˜2.77 (m, 1H), 2.60˜2.64 (m, 1H), 2.29˜2.35 (m, 1H), 2.02˜2.10 (m, 1H), 1.03 (d, 6.6 Hz, 3H), 0.91 (d, 6.7 Hz, 3H).

Provenance & Evidence