Methyl iodide → (7aR)-Tetrahydro-3,3,6,6-tetramethyl-3H,5H-pyrrolo[1,2-c]oxazol-5-one

To a solution of (R)-3,3-dimethyltetrahydropyrrolo[1,2-c]oxazol-5(3H)-one (D34) (1.3 g, 8.37 mmol) in dry THF (120 ml) cooled to −78° C., LDA 2M sol in THF/heptane (6.28 ml, 12.6 mmol) was added. The red solution was stirred at this temperature for 40 min before adding iodomethane (0.78 ml, 12.6 mmol). The reaction mixture was warmed to RT (40 min) then cooled to −78° C. prior addition of LDA 2M sol in THF/heptane (6.28 ml, 12.6 mmol). The mixture was stirred at −78° C. for 1 h before adding iodomethane (0.78 ml, 12.6 mmol) then the mixture was slowly warmed to RT and stirred overnight. The resulting solution was treated with NH4Cl sat sol (10 ml) and extracted with Et2O (3×10 ml). The organic phases were collected and washed with NaCl sat. sol, dried over Na2SO4 and evaporated in vacuo to afford the title compound (D35) (1.2 g).

1. additionwas added
2. temperaturethen cooled to −78° C.
3. stirringThe mixture was stirred at −78° C. for 1 h
4. temperaturethe mixture was slowly warmed to RT
5. stirringstirred overnight
6. extractionextracted with Et2O (3×10 ml)
7. customThe organic phases were collected
8. washwashed with NaCl sat. sol
9. dry with materialdried over Na2SO4
10. customevaporated in vacuo

ORD record

ord-802834eac6e54ba3a777af0e1400a740

Source dataset

uspto-grants-2015_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09181279B2