Diisobutylaluminumhydride → HCID 10514391, compound

Participants

Reaction Conditions

Reaction Steps

A solution of the resultant compound of Example 30 (3.25 g, 14.4 mmol) in anhydrous tetrahydrofuran was cooled to -78° C. and treated slowly along the side of the reaction vessel with 57 ml (57 mmol) of diisobutylaluminum hydride (1M in tetrahydrofuran). The solution was stirred at -78° C. for 0.5 h, quenched cautiously with methanol, allowed to warm to ambient temperature, and partitioned between ether and aqueous Rochelle salts. The organic phase was washed sequentially with water and brine, dried over MgSO4, and concentrated in vacuo. Chromatography on silica gel using 4:1 hexane:ethyl acetate provided 0.77 g (22%) of the desired compound (10:1 ratio of (3S,4S):(3R:4S) isomers). 1H NMR (CDCl3) δ 0.91 (d, J=7 Hz 3 H), 0.94 (d, J=7 Hz, 3 H), 1.26 (br t, J=7 Hz, 2 H), 1.44 (s, 9 H), 1.67 (nonet J=7 Hz, 1 H), 2.96 (br d, J=5 Hz, 1 H), 3.82 (m, 1 H), 4.18 (m, 1 H), 4.50 (br d, 1 H), 5.23 (dt, J=11, 1.5 Hz, 1 H), 5.33 (dt, J=17, 1.5 Hz, 1 H), 5.84 (ddd, J=17, 11, 6 Hz, 1 H).

Provenance & Evidence