HCID 14016132, compound → HCID 11153871, compound

Participants

Reaction Steps

A solution comprising 2.49 g (6.08 mmole) of tert-Butyl (1S, 2S)-N-[2-hydroxy-1-(hydroxymethyl)-3-heptadecynyl]carbamate, Herold, Chim. Acta. 71: 354, 1988, and 20 mg of 20% Pd on carbon in 50 ml of ethyl acetate was hydrogenated on a Parr shaker at 3 atmospheres for 3 hours. The reaction mixture was filtered through Celite and the solvent removed under reduced pressure yielding tert-Butyl (1S, 2S)-N-[2-hydroxy-1-(hydroxymethyl) heptadecyl]carbamate having a mass of 2.53 g and of approximately 100%. Tert-Butyl (1S, 2S)-N-[2-hydroxy-1-(hydroxymethyl) heptadecyl]carbamate is a wax having a melting point of approximately 45° to 56° C. A 1H NMR analysis of the compound at 300 MHz using CDCl3 comprised the following peaks: δ0.887 (3H, t, J=6.7 Hz), 1.261 (26H, bs), 1.460 (9H, s), 2.054 (2H, bs), 3.589 (1H, bs), 3.820 (2H, bs), 3.941 (1H, bs) and 5.232 (1H, d, J=8.0 Hz). E;elemental analysis calculated for C23H47NO4 comprised the following constituents: C: 68.78, H: 11.79, N: 3.49. The values obtained experimentally comprised: C: 68.46,H: 11.71, N: 3.44.

Provenance & Evidence