Aluminium lithium hydride → HCID 69055105, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (±)-trans-2-benzyl-6-methyl-2,3,3a,4-tetrahydro-1H-pyrrolo[3,4-c]isoquinolin-5(9bH)-one, from Example 101, Part A, (830 mg, 2.84 mmol) in 20 mL of THF was added lithium aluminum hydride (3.4 mL of a 1 M solution in THF, 3.4 mmol). The reaction was heated in a microwave oven at 100° C. for 1.5 h. The reaction was cooled, filtered through a pad of silica gel with 10% methanol/methylene chloride, and concentrated in vacuo. The residue was purified (ISCO, elution with 0-12% methanol/methylene chloride) to afford 345 mg (44%) of the title compound as a solid. 1H NMR (CDCl3): δ 7.40-7.25 (m, 5H), 7.08-6.98 (m, 2H), 6.80 (d, 1H), 4.12 (ABq, 2H), 3.87 (ABq, 2H), 3.42-3.37 (m, 1H), 3.15-3.06 (m, 2H), 2.98-2.90 (m, 1H), 2.80-2.71 (m, 2H), 2.17 (s, 3H). LRMS (ESI): 279.2 (M+H)+.

Provenance & Evidence