HCID 89573786, compound → HCID 89260757, compound

Participants

Reaction Steps

10% Palladium on carbon (54 mg, 0.051 mmol) was added to a flask charged with a solution of tert-butyl rel-((4aS,10bS)-9-azido-10b-methyl-4a,5,6,10b-tetrahydro-4H-naphtho[1,2-d][1,3]thiazin-2-yl)carbamate from step D1 (190 mg, 0.509 mmol) in methanol (40 mL) under dry nitrogen. The vessel was repeatedly flushed with hydrogen gas. The reaction mixture was allowed to stir under a balloon of hydrogen gas for 20 h. The vessel was flushed with nitrogen. The contents were filtered through celite. The celite and vessel were rinsed with methanol. The combined filtrates were concentrated in vacuo. The residue was dried under high vacuum to afford tert-butyl((4aS,10bS)-9-amino-10b-methyl-4a,5,6,10b-tetrahydro-4H-naphtho[1,2-d][1,3]thiazin-2-yl)carbamate (180 mg, 0.518 mmol, 100% yield) as a gray oil. LCMS (M+Na)+=270.1. 1H NMR (500 MHz, chloroform-d) δ 6.89 (d, J=8.1 Hz, 1H), 6.81-6.72 (m, 1H), 6.58 (dd, J=8.1, 2.4 Hz, 1H), 3.66 (br. s, 2H), 3.03 (dd, J=13.0, 3.7 Hz, 1H), 2.92 (dd, J=12.9, 8.3 Hz, 1H), 2.77 (t, J=6.9 Hz, 2H), 2.26 (dt, J=7.2, 3.6 Hz, 1H), 2.11 (dtd, J=14.0, 7.1, 3.6 Hz, 1H), 1.97 (dq, J=13.7, 6.7 Hz, 1H), 1.63 (s, 3H), 1.49 (s, 9H).

Provenance & Evidence