Water → HCID 23198943, compound

Participants

Reaction Conditions

Reaction Steps

Ice cold sodium hydroxide solution (75 mL, 2N) was added to hydroxylamine-O-sulfonic acid (17.1 g, 0.15 mol) in water (150 mL) at 0° C. When the solution had cooled to about 5° C. it was added in one portion to a mixture of sodium hydroxide solution (75 mL, 2N), cyclohexanone (15 g, 0.15 mol) and toluene (270 mL) at 0° C. The mixture was stirred for 10 min. The organic layer was separated, dried and decanted from the drying agent. This afforded a solution of the cyclohexane-spiro-3'-oxaziridine which was used directly. The oxyaziridine solution prepared as above (540 mL) was added in one portion to an enolate (previously prepared by addition of 2-methyl-6-chlorotetralone (18.07 g, 92.9 mmol) in THF (40 mL) to lithium diisopropylamide (10.4 g, 97.1 mmol) in THF/hexanes (60 mL/40 mL) at -50° C. When the addition was complete, the mixture was stirred for 1 h at -50° C.). The reaction was stirred for 1 h, and was allowed to warm to 0° C. The mixture was poured into water (500 mL), and the organic layer was separated. The aqueous layer was further extracted with dichloromethane (3×250 mL). The combined extracts were dried, hydrochloric acid (about 10 mL, conc.) was added, and the mixture was evaporated. Ether (250 mL) was added and hydrochloric acid (about 10 mL, conc.) was added. The mixture was stirred overnight and was filtered to give the product as a solid (19.18 g, 83%). 1H NMR (free base) (CDCl3) δ8.00 (d, 1H), 7.32-7.25 (m, 2H), 3.19-2.89 (m, 2H), 2.18-1.98 (m, 2H), 1.29 (s, 3H).

Provenance & Evidence