Water → HCID 23198943, compound

Temperature

-50 °C

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).

1. additionWhen the addition
2. stirringThe reaction was stirred for 1 h
3. temperatureto warm to 0° C
4. customthe organic layer was separated
5. extractionThe aqueous layer was further extracted with dichloromethane (3×250 mL)
6. customThe combined extracts were dried
7. additionhydrochloric acid (about 10 mL, conc.) was added
8. customthe mixture was evaporated
9. additionEther (250 mL) was added
10. additionhydrochloric acid (about 10 mL, conc.) was added
11. stirringThe mixture was stirred overnight
12. filtrationwas filtered

ORD record

ord-1651f0d99403472fa8f2fc0490f3cdfe

Source dataset

uspto-grants-1996_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05514678