Carbon Tetrachloride → 7-(Benzyloxy)-5-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2,3,4-tetrahydro-5H-naphtho[1,2-b]azepine

Participants

Reaction Conditions

Reaction Steps

A solution of 83 (0.105 g, 0.24 mmol, 1 equiv) in CH2Cl2 (2 mL) was treated with CCl4 (0.225 mL, 2.33 mmol, 9.7 equiv) followed by Ph3P (0.212 g, 0.81 mmol, 3.3 equiv) and the mixture was stirred at 25° C. for 2.5 h. The crude reaction solution was passed through a plug of silica gel and concentrated. Radial chromatography (SiO2, 1 mm plate, 5% EtOAc-hexane) provided 86 as a pale yellow oil (0.048 g, 0.108 g theoretical, 44%): 1H NMR (250 MHz, CDCl3) major rotamer δ 8.44-8.36 (m, 1H), 8.15-7.12 (m, 1H), 7.62-7.33 (m, 7H), 6.64 (s, 1H), 5.31-5.15 (m, 2H), 4.46-4.41 (m, 1H), 4.17-4.08 (m, 1H), 3.92-3.81 (m, 1H), 3.74-3.63 (m, 1H), 2.78-2.69 (m, 1H), 2.41-2.35 (m, 1H), 2.17-2.05 (m, 1H), 1.72-1.67 (m, 2H), 1.30 (s, 9H); IR (film) νmax 2971, 2930, 2859, 1693, 1617, 1592 cm−1; FABHRMS (NBA-NaI) m/z 451.1933 (M+, C27H30CINO3 requires 451.1914).

Provenance & Evidence