Triphenylphosphine → HCID 68069234, compound

Participants

Reaction Conditions

Reaction Steps

In a 40 mL vial, 6-hydroxy-2-methyl-2H-benzo[b][1,4]oxazin-3(4H)-one 394C (0.200 g, 1.116 mmol), tert-butyl 4-hydroxypiperidine-1-carboxylate (0.225 g, 1.116 mmol), and PPh3 (0.439 g, 1.674 mmol) were suspended in THF (5.58 mL) to give a brown solution. The mixture was cooled to 0° C. To the cooled mixture was added DEAD drop-wise. The reaction was slowly warmed to 23° C. and stirred for 18 hr. The crude material was purified by prep HPLC-MS (45-85% MeCN in water). The fractions were collected and concentrated in vacuo to give the title compound (0.223 g, 55.1% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 1.33-1.44 (m, 9H) 1.44-1.59 (m, 2H) 1.86 (ddd, J=9.47, 6.32, 3.16 Hz, 2H) 3.06-3.24 (m, 2H) 3.33-3.71 (m, 5H) 4.32-4.44 (m, 1H) 4.57 (q, J=6.65 Hz, 1H) 6.48 (d, J=2.78 Hz, 1H) 6.55 (dd, J=8.84, 2.78 Hz, 1H) 6.86 (d, J=8.59 Hz, 1H) 10.56 (s, 1H). ESI-MS: m/z 307.2 and 263.2 (M+H)+.

Provenance & Evidence