HCID 131727758, compound → HCID 131727760, compound

Participants

Reaction Steps

To a solution of (±)-cis tert-butyl 6-methyl-4-oxo-3,3a,4,5-tetrahydro-1H-pyrrolo[3,4-c]quinoline-2(9bH)-carboxylate from Example 18, Part A (2.4 g, 8 mmol) in 60 mL of THF at 0° C. was added borane THF complex (40 mL of a 1 M solution in THF, 40 mmol) dropwise. The reaction was allowed to warm to ambient temperature and was stirred for 2 h. The reaction was quenched carefully with water and extracted with ethyl acetate. The organics were washed with brine, dried (Na2SO4) and concentrated in vacuo. The residue was purified by flash chromatography to afford 1.55 g (67%) of the title compound. 1H NMR (CDCl3) (some signals doubled due to rotamers): δ 6.95-6.90 (m, 1H), 6.65-6.57 (m, 1H), 4.00-2.93 and 3.87-3.80 (m, 1H), 3.66-3.58 (m, 1H), 3.42-2.98 (m, 5H), 2.58-2.44 (m, 1H), 2.11 (s, 3H), 1.44 and 1.43 (s, 9H).

Provenance & Evidence