Aluminium lithium hydride → HCID 21341515, compound

Participants

Reaction Conditions

Reaction Steps

A cold (−40° C.) solution of lithium aluminum hydride (25.2 mL of a 1M solution, 1.2 eq.) in tetrahydrofuran (165 mL), under nitrogen, was treated with a solution of N-tert-Butoxycarbonyl-D-homophenylalanine methoxymethylamide (6.76 g, 20.9 mmol) in tetrahydrofuran (20 mL) at such a rate as to keep the temperature between −36 to −38° C. After the addition, the temperature was allowed to rise to 7° C. after which the reaction mixture was cooled to −35° C. The mixture was quenched with 2.75M KHSO4 solution and stirred for 1 h whilst warming to 25° C. The aqueous layer was separated and extracted thrice with ether. The combined organics were washed successively thrice with 10% citric acid, water, saturated bicarbonate and brine, dried (MgSO4) and concentrated. The viscous clear residue solidified under vacuum, giving the title compound (5.32 g): 1H NMR (400 MHz, CDCl3) δ 1.47 (s, 9H), 1.88 (m, 1H), 2.22 (m, 1H), 2.71 (t, J=7.6 Hz, 2H), 4.24 (m, 1H), 5.18 (bd, 1H, NH), 7.20 (m, 3H), 7.27 (m, 2H) and 9.54 (s, 1H).

Provenance & Evidence