Trifluoroacetic acid → (S)-3-(Azidomethyl)-1,2,3,4-tetrahydroisoquinoline

Participants

Reaction Steps

To a solution of (S)-tert-butyl 3-(azidomethyl)-3,4-dihydroisoquinoline-2(1H)-carboxylate (Page, D. et al., J. Med. Chem., 44:2387-2390 (2001)) (509 mg, 1.77 mmol) in CH2Cl2 (8.0 mL) was added TFA (2.7 mL, 35.3 mmol). The resulting reaction mixture was stirred at room temperature for 1 h and then concentrated in vacuo. The residue was dissolved in CH2Cl2 and washed with sat. aq. NaHCO3 solution (2×). The aqueous layer was extracted with CH2Cl2 (2×), and the combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to provide the title compound (302 mg, 91%) as a clear, colorless oil. 1H NMR (CDCl3) δ 7.17-7.13 (m, 2H), 7.12-7.08 (m, 1H), 7.07-7.02 (m, 1H), 4.14-4.05 (m, 2H), 3.55 (dd, J=12.2, 4.4 Hz, 1H), 3.45-3.39 (m, 1H), 3.16-3.09 (m, 1H), 2.82-2.75 (m, 1H), 2.70-2.60 (m, 1H), 2.02 (br s, 1H); MS(ESI+) m/z 189.1 (M+H)+.

Provenance & Evidence