Chlorosuccinimide → HCID 86622735, compound

Participants

Reaction Steps

To a mixture of tert-butyl 4-{[(4-{[trans-2-hydroxycyclopentyl]oxy}-1,2-benzisoxazole-3-yl)oxy]-methyl}piperidine-1-carboxylate (158 mg, 0.365 mmol, EXAMPLE 32, step 1), 2,2,6,6-tetramethyl-1-piperidinyloxy (TEMPO, 2.4 mg, 0.015 mmol), sodium bicarbonate (98.3 mg, 1.17 mmol), and tetra-n-butylammonium bromide (8.2 mg, 0.025 mmol) in dichloromethane (2 mL) and water (0.4 mL) was added N-chlorosuccinimide (60.3 mg, 0.453 mmol) at ambient temperature. After being stirred for 4 h, the mixture was quenched with aq. sodium thiosulfate. The mixture was extracted with ethyl acetate (20 mL) and washed with aq. potassium carbonate and brine. The extract was dried over magnesium sulfate and concentrated in vacuo to give 167 mg (crude mixture) of the title compound.

Provenance & Evidence