Aluminium lithium hydride → HCID 67166624, compound

Participants

Reaction Steps

A solution of the product from Example 107D (695 mg, 2.46 mmol) in 10 mL of tetrahydrofuran was chilled to −70° C. under nitrogen and treated dropwise with lithium aluminum hydride (5.0 mL of a 1.0 M solution in tetrahydrofuran). After the addition was completed the reaction was allowed to warm to room temperature over 3 hours and then quenched with 5 mL of ethyl acetate followed by 15 mL of 2 N aqueous hydrochloric acid solution. The layers were separated and the aqueous portion was extracted with 4×10 mL of ethyl acetate and the combined organic extracts were dried over sodium sulfate. The organic solution was concentrated and the residue was purified via flash chromatography on a silica gel column (100%) ethyl acetate to afford the title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.71 (dd, J=12.89, 2.03 Hz, 1H) 2.01-2.15 (m, 2H) 2.86 (td, J=7.71, 3.90 Hz, 1H) 3.16-3.29 (m, 2H) 3.52 (ddd J=10.51, 7.12, 5.43 Hz, 1H) 3.66-3.78 (m, 2H) 4.12 (dt, J=12.12, 4.11 Hz, 1H) 4.48 (t, J=5.09 Hz, 1H) 4.59 (t, J=5.43 Hz, 1H) 6.71 (dd, J=10.17, 2.71 Hz, 1H) 6.81 (td, J=8.31, 2.71 Hz, 1H) 7.12 (dd, J=8.48, 6.78 Hz, 1H); MS (DCI+) m/z 226.1 [M+NH4]+.

Provenance & Evidence