Reaction #172120

Reaction equation

solution

Trans-tert-butyl 6-oxo-1,3a,4,5,6,10b-hexahydrobenzo[c]pyrrolo[3,4-e]azepine-2(3H)-carboxylate

lithium aluminum hydride

Water

→

title compound

Trans-2-methyl-1,2,3,3a,4,5,6,10b-octahydrobenzo[c]pyrrolo[3,4-e]azepine

Solvents

tetrahydrofuran

tetrahydrofuran

Conditions

Workup

1. 1
   Extractionthe product was extracted once with dichloromethane
2. 2
   Dryingdried over Na2SO4
3. 3
   Concentrationconcentrated

Procedure

To a solution of Example 71A (2.62 g, 8.66 mmol) in tetrahydrofuran (87 mL) was added lithium aluminum hydride in tetrahydrofuran (13.00 mL, 26.0 mmol) in small portions, and the mixture was stirred at room temperature for 24 hours. Water was added carefully and the product was extracted once with dichloromethane, dried over Na2SO4 and concentrated to afford the title compound. 1H NMR (500 MHz, pyridine-d5) δ ppm 7.31 (d, J=7.4, 1H), 7.20-7.17 (m, 2H), 7.13 (d, J=7.7, 1H), 4.58 (dd, J=14.5, 48.4, 2H), 4.01-3.90 (m, 2H), 3.71-3.57 (m, 2H), 3.40 (t, J=10.4, 1H), 3.19-3.05 (m, 2H), 2.71 (s, 3H), 2.66-2.52 (m, 1H); MS (ESI+) m/z 203.0 [M+H]+.

Source