Methanol → Trans-6-[4'-(3-Fluoro-1(Z)-propenyl)phenyl]-1,2,3,5,6,10b-Hexahydropyrrolo[2,1-a]isoquinoline

Participants

Reaction Steps

To a stirred solution of 1.0 M tetrabutylamonium fluoride (0.45 mL, 0.45 mmol) in 2.0 mL of THF in the presence of molecular sieves (4 Å, 1.0 g) was added a mixture of methylsufonyl fluoride (21 μL, 0.30 mmol) and trans-1,2,3,5,6,10b-Hexahydro-6-[4'-(3-hydroxy-1(Z)-propenyl)phenyl]pyrrolo[2,1-a]isoquinoline (18) (23 mg, 0.075 mmol) in 5 mL of THF at room temperature. The reaction mixture was heated at reflux for 16 h, cooled to room temperature, filtered through a sintered glass funnel with aid of a small amount of methylene chloride (10 mL) and ethyl acetate (10 mL). The filtrate was concentrated to afford a crude product. Flash chromatography with 2.3% MeOH, 0.046% Et3N in methylene chloride gave 10 mg of thick colorless oil (43% yield). 1H NMR (CDCl3) δ 1.73-2.05 (m, 3H, C2H2 & C1H), 2.30-2.2.44 (m, 1H, C1H), 2.579 (dt, 1H, J=9.0, 8.7 Hz, C3H), 2.869 (dd, 1H, J=5.1, 11.1 Hz, C5H), 2.90-3.03 (m, 2H, C3H & C5H), 3.480 (dd, 1H, J=7.2, 9.0 Hz, C10bH), 4.125 (t, 1H, J=4.8 Hz, C6H), 6.865 (d, 1H, J=7.5 Hz, aryl), 6.995 (d, 2H, J=8.1 Hz, C6 phenyl aryl), 7.04-7.20 (m, 3H, aryl), 7.575 (d, 2H, J=8.1 Hz, C6 phenyl aryl) (aromatic), 126.30, 129.30, 130.97, 137.23.

Provenance & Evidence