Phenol → HCID 68108517, compound

Participants

Reaction Steps

The product of step C (150 mg, 0.37 mmol) was converted to the phenol derivative following the procedure of Example 54, step A. The crude product was purified by column chromatography (SiO2, 4:1 hexanes/ethyl acetate) providing tert-butyl 8-benzyl-6-hydroxy-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (100 mg, 71%) as an off-white solid which was converted directly to the methyl ether derivative following the procedure of Example 54, step B. Purification by column chromatography (SiO2, 85:15 hexanes/ethyl acetate) provided tert-butyl 8-benzyl-6-methoxy-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (80 mg, 58%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 7.32-7.27 (m, 2H), 7.23-7.16 (m, 3H), 6.84 (br s, 1H), 6.61 (s, 1H), 4.50 (br s, 2H), 4.04 (s, 2H), 3.95 (s, 3H), 3.80 (t, J=5.4 Hz, 2H), 2.88-2.81 (m, 2H), 1.49 (s, 9H).

Provenance & Evidence