Trisodium Phosphate → (3E)-3-Dibenz(b,e)oxepin-11(6H)-ylidene-N-methyl-1-propanamine

Participants

Reaction Steps

The N-protected (E)-desmethyldoxepin intermediate (1.44 g, 3.27 mmol) was dissolved in 12 mL THF, 2.88 g of zinc powder added, 2.3 mL of 1M sodium phosphate (pH=5.5) added, and reaction stirred for 17 hours. The reaction mixture was then vacuum filtered, filtrate solvent removed in vacuo, and resulting residue purified by silica gel column chromatography, eluting with THF/MeOH/NH4OH (85/15/0.4), then THF/MeOH/NH4OH (75/25/0.4), to afford 744 mg (2.80 mmol) of the desired product [3] as a pale yellow solid; 1H NMR (200 MHz, CDCl3): d 2.5 (s, 3H), 2.7 (m, 2H), 3.0 (m, 2H), 4.7-5.8 (broad s, 2H), 6.0 (t, 1H), 6.8-6.9 (m, 2H), 7.1-7.4 (m, 6H); mass spec (FAB): (M+H)+266.

Provenance & Evidence