Hydrochloric Acid → HCID 22851794, compound

Participants

Reaction Steps

To a solution of trans-1-p-methoxybenzyloxycarbonyl-4-hydroxyproline (105.5 g: 357.5 mmole) in tetrahydrofuran (1 liter), triethylamine (54.8 ml) is added. After adding ethyl chloroformate (35.9 ml) dropwise at -30° C., the mixture is stirred for 20 minutes. To the reaction mixture, a solution of sodium borohydride (33.25 g) in water (120 ml) is added dropwise at a temperature in the range of -15° to -5° C., neutralized with conc. hydrochloric acid, and concentrated in vacuo. To the residue, ethyl acetate is added, washed with brine, dried over magnesium sulfate, and concentrated in vacuo to give (2S,4R)-1-p-methoxybenzyloxycarbonyl-4-hydroxy-pyrrolidine-2-methanol. NMR δ(CDCl3) ppm: 1.6 to 1.8(m, 1H), 1.95 to 2.2(m, 1H), 3.4 to 3.8 (m, 4H), 3.8(s, 3H), 4.0 to 4.3(m, 1H), 4.37(br s, 1H), 5.07(s, 2H), 6.88(d, J=8.8 Hz, 2H), 7.30(d, J=8.8 Hz, 2H).

Provenance & Evidence