(R)-Tert-butyl (4-fluoro-1-hydroxy-4-methylpentan-2-YL)carbamate → 4-fluoro-4-methyl-1-(5-methyl-5H-chromeno[3,4-c]pyridin-8-yloxy)pentan-2-amine

Participants

Reaction Steps

Prepared as described in Example 8, Part D using 8-chloro-5-methyl-5H-chromeno[3,4-c]pyridine (0.100 g, 0.432 mmol) and tert-butyl(4-fluoro-1-hydroxy-4-methylpentan-2-yl)carbamate (0.168 g, 0.712 mmol) to afford 4-fluoro-4-methyl-1-(5-methyl-5H-chromeno[3,4-c]pyridin-8-yloxy)pentan-2-amine (80 mg, 0.23 mmol, 99% yield) as a yellow oil. 1H NMR (400 MHz, MeOD) δ 8.66 (d, J=6.4 Hz, 1 H), 8.64 (s, 1 H), 8.24 (d, J=6.4 Hz, 1 H), 8.08 (d, J=8.8 Hz, 1 H), 6.94 (dd, J=2.4 Hz, 8.8 Hz, 1 H), 6.78 (d, J=2.8 Hz, 1 H), 5.57 (q, J=6.4 Hz, 1 H), 4.38 (dd, J=6.4 Hz, J=10.8 Hz,1 H), 4.22 (dd, J=6.4 Hz, 10.8 Hz, 1 H), 3.99 (m, 1 H), 2.16 (m, 2 H), 1.75 (d, J=6.8 Hz, 3 H), 1.55 (s, 3 H), 1.50 (s, 3 H); LCMS (ESI) m/e 331.2 [(M+H)+, calcd for C19H24FN2O2331.2] LC/MS retention time (method D): tR=0.97 min; HPLC retention time (method B): tR=8.04 min.

Provenance & Evidence