Aluminium lithium hydride → HCID 66941293, compound

Participants

Reaction Steps

To a 0° C. suspension of compound 32 (1.153 g, 3.62 mmol) in dry THF (60 mL) on ice was added LiAlH4 (0.566 g, 14.89 mmol). The mixture was then heated at reflux for 2 h. The solution was cooled, stirred 1 h then the excess LiAlH4 was quenched by the sequential addition of 0.6 mL water, 1.2 mL 4 M NaOH solution and 0.6 mL water. The solids that formed will filtered (Celite) and the filtrate concentrated to give 33 as a pale colored oil (1.076 g, 99% yield). 1H NMR (400 MHz, CDCl3): δ 1.44-1.62 (m, 4H), 1.64-1.74 (m, 1H), 1.74-1.94 (m, 2H), 2.08-2.17 (m, 1H), 2.35 (bs, 1H, NH), 2.71-2.79 (m, 2H), 2.87-2.95 (m, 1H), 2.95-3.08 (m, 2H), 3.26 (m, 0.5H), 3.36 (dd, J=4.0, 9.9 Hz, 0.5H), 3.45-3.52 (m, 3H), 3.61-3.73 (m, 1H), 3.78-3.86 (m, 1H), 4.56 (m, 1H); 3C NMR (100 MHz, CDCl3): δ 19.4, 19.5, 25.3, 30.5, 45.1, 53.4, 53.5, 54.5, 54.7, 55.7, 62.2, 62.4, 63.3, 69.5, 69.9, 98.8, 99.5, 127.0, 128.2, 129.1, 137.9.

Provenance & Evidence