HCID 18782843, compound → HCID 18782848, compound

Participants

Reaction Steps

2-Ethyl-6,6-dimethyl-bicyclo[3.1.1]heptane-3-carbonitrile (288 mg, 1.65 mmol) was dissolved in anhydrous THF (10 ml) under an atmosphere of dry N2. To the reaction was added a 1.0 M solution of lithium aluminum hydride (4.0 ml) in THF. The reaction was stirred at ambient temperature for 16 hr and was then quenched by the sequential slow addition of 152 μl of water, 152 μl of 15% NaOH and finally 460 μl of water. The reaction was stirred for an additional 2 hr after which time it was filtered and the filter cake was washed with CH 2Cl2. The combined filtrate was concentrated under vacuum to give 267 mg of the titled compound: 1H NMR (CD3OD) 6 2.73 (dd, J=4.6,12.2 Hz, 1H), 2.41 (dd, J=9.5, 12.2 Hz, 1H), 2.32 (m, 1H), 2.19 (m, 1H), 1.98 (m, 1H), 1.91 (m, 1H), 1.74 (m, 1H), 1.28-1.57 (m, 4H), 1.20 (s, 3H), 0.99 (s, 3H), 0.89 (t, J=7.2 Hz, 3H), 0.74 (d, J=9.6 Hz, 1H).

Provenance & Evidence