Ether hydrochloride → HCID 70404184, compound

Participants

Reaction Steps

N-Benzyloxycarbonyl-D-alanine 1-adamantyl ester (7.35 g, 20.6 mmol) was dissolved in 100 mL MeOH and 14.5 mL 1.25N HCl/ether. The solution was hydrogenated over 1.09 g of 10% Pd/C at 40 psi in a Parr apparatus at room temperature for 40 minutes. The solution was filtered through a Celite pad and the clear filtrate was evaporated to dryness to give a yellow oil, which was crystallized from EtOAc. A light yellow salt (4.2 g) was obtained. The crude product was recrystallized from MeOH-EtOAc; yielded 7.85 g (72%), mp 218°-219° (dec), 250 MHz nmr (CD3OD, ppm) 1.50 (d, 3H, J=7.35 Hz, β--CH3 of Ala), 1.72 (m, 6H, 1-adamantyl aliphatic protons of C's 2, 8 and 9), 2.18 (m, 9H, adamantyl aliphatic protons), 3.95 (q, 1H, J=7.35 Hz, α--H of Ala).

Provenance & Evidence