Triphenylphosphine → HCID 59596700, compound

Participants

Reaction Conditions

Reaction Steps

Polystyrene supported PPh3 (100 mg, 1.5 mmol) and DIAD (30 mg, 1.5 mmol) were added to a solution of 1,1-dimethylethyl (2S,5R)-2-(aminocarbonyl)-5-(4-hydroxyphenyl)-1-pyrrolidinecarboxylate (D13, 30 mg, 0.10 mmol) in dry THF (1 ml) at 0° C. After 15 min (1R)-1-phenylethanol (24.4 mg, 0.2 mmol) was added and the reaction mixture was stirred at 0° C. for 2 h. The resin was filtered off and the solvent was evaporated. The crude material was purified by chromatography on silica gel using cyclohexanes/ethyl acetate (8:2) to afford the title compound (20 mg, 48%); Rt (HPLC): 5.70 min, 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 1.31 (s, 9H); 1.53 (d, 3H); 1.65-1.78 (m, 1H); 1.79-1.92 (m, 1H); 1.93-2.03 (m, 1H); 2.07-2.21 (m, 1H); 4.50 (br. s., 1H); 4.70 (br. s., 1H); 5.41-5.50 (m, 1H); 6.78 (d, 2H); 6.91 (s, 1H); 7.23 (br. s., 1H); 7.31 (br. s., 2H); 7.39 (br. s., 4H); 7.44 (br. s., 1H).

Provenance & Evidence