Benzyl Bromide → (1R*,4S*)-6-allyl-5-(benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene

Participants

Reaction Steps

Treatment of (1R*,4S*)-6-allyl-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalen-5-ol (14.2 g, 61.66 mmol) with potassium carbonate (34.09 g, 0.247 mol), benzyl bromide (11.07 g, 64.74 mmol), and tetrabutylammonium iodide (0.224 g, 6.166 mmol) generally according to the procedure described for Intermediate 1 provided 17.86 g (90%) of (1R*,4S*)-6-allyl-5-(benzyloxy)-8-methoxy-1,2,3,4-tetrahydro-1,4-methanonaphthalene as a colorless oil. Anal. calcd. for C22H2402-0.5H2O: C, 80.21; H, 7.65. Found: C, 79.81; H, 7.48.

Provenance & Evidence