Boc-Hyp(Bzl)-OH → HCID 14821719, compound

Participants

Reaction Conditions

Reaction Steps

(2S,4R)-4-Benzyloxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester (960 mg, 3 mmol) in THF (5 mL) was cooled to 0° C. using ice-water bath. Then 1M solution of BH3 (6mL, 6 mmol) in THF was added under nitrogen over period of 30 min. Reaction was stirred at 0° C. for 2 h and at rt for another 1 h. Reaction mixture was poured over ice water and product was extracted with EtOAc. Organic layers were combined, washed with water, brine, saturated sodium bicarbonate, dried over anhydrous MgSO4 and concentrated to give the crude product. It was used in next step without purification (900 mg, 97%); MS; m/z 286.1 (M+H); 1H NMR (400 MHz, DMSO-4-d6); δ 1.90 (m, 1H), 2.01 (m, 1H), 3.09 (m, 1H), 3.34 (m, 1H), 4.12 (m, 2H); 4.27 (m, 1H), 4.46 (m, 1H), 5.46 (br s, 2H), 6.92 (d, J=6.8 Hz, 2H), 7.02 (s, 4H), 7.08 (t, J=5.6 Hz, 1H), 7.35 (m, 2H), 9.09 (br s, 1H), 9.62 (br s, 3H);

Provenance & Evidence