Methanol → [1R,3S] 1-Aminomethyl-5-hydroxy-3-phenyl-1,2,3,4-tetrahydronaphthalene formic acid salt

Temperature

-78 °C

[1R,3S] 1-Aminomethyl-5-methoxy-3-phenyl-1,2,3,4-tetrahydronaphthalene hydrochloride (0.16 g, 0.53 mmol), from Step 1, was suspended in 5 mL of methylene chloride and the suspension was cooled to -78° C. in a dry ice/acetone bath. Boron tribromide (19 mL of a 1 M solution in methylene chloride, 19 mmol) was added and the reaction mixture was allowed to warm to ambient temperature, kept at ambient temperature for 1.5 h then cooled to -78° C. Methanol (3 mL) was added to the reaction mixture and it was again allowed to warm to ambient temperature then concentrated in vacuo. The residue was dissolved in methanol and reconcentrated. The residue was redissolved in methanol and the methanol solution was chromatographed on a silica gel column eluted with ethyl acetate:formic acid:water (18:1:1, v/v/v) to give 0.11 g (70% yield) of the title compound as a white powder, m.p. 110°-112° C.; 1H NMR (d6 -DMSO) δ1.7 (q, 1H), 2.1-2.25 (m, 1H), 2.35-2.5 (m, 1H), 2.75-2.90 (m, 2H), 2.9-3.05 (m, 1H), 3.05-3.2 (m, 1H), 3.25-3.35 (m, 1H), 6.07 (d, 1H), 6.81 (d, 1H), 7.0 (t, 1H), 7.2-7.3 (m, 1H), 7.3-7.4 (m, 4H), 8.38 (s, 1H).

1. temperatureto warm to ambient temperature
2. temperaturethen cooled to -78° C
3. temperatureto warm to ambient temperature
4. concentrationthen concentrated in vacuo
5. dissolutionThe residue was dissolved in methanol
6. dissolutionThe residue was redissolved in methanol
7. customthe methanol solution was chromatographed on a silica gel column
8. washeluted with ethyl acetate:formic acid:water (18:1:1, v/v/v)

ORD record

ord-77cc17c6ee2f4b9f9f2258d7588210bc

Source dataset

uspto-grants-1991_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04994486