N-Hydroxyphthalimide → HCID 57461145, compound

Participants

Reaction Steps

4-Hydroxy-piperidine-1-carboxylic acid isopropyl ester (3.09 g, 17 mmol), N-hydroxyphthalimide (2.69 g, 17 mmol), and triphenylphosphine (4.32 g, 17 mmol) were combined in THF (30 mL). DEAD (2.6 mL, 17 mmol) was added and the mixture was stirred at room temperature for 18 h. The mixture was then concentrated under vacuum and the residue was purified by flash LC(elution with 10-50% ethyl acetate and 0.1% TEA in hexanes) to afford 3.31 g (60%) of 2a as a colorless oil: 1H NMR (300 MHz, CDCl3) δ 7.85-7.81 (m, 2 H), 7.83-7.29 (m, 2 H), 4.91 (quintet, J=6.3 Hz, 1 H), 4.43 (septet, J=3.9 Hz, 1 H), 3.94-3.86 (m, 2 H), 3.32-3.23 (m, 2 H), 1.99-1.78 (m, 4 H), 1.24 (d, J=6.6 Hz, 6 H); LC-MS 333.1 (MH+).

Provenance & Evidence