Diisopropylamine → HCID 59438453, compound

Temperature

0 °C

To a solution of 118 ul (0.833 mmol) diisopropylamine in 3 ml THF were added 520 ul (0.833 mmol) of a 1.6M n-BuLi solution in hexane at −5° C. The solution was stirred for 15 minutes at 0° C. and then cooled to −70° C. A solution of 150 mg (0.641 mmol) rac-1-methyl-5-nitro-5-phenyl-piperidin-2-one (example A.9, step 1) in 1.5 ml THF was added dropwise. The brown solution was stirred at −70° C. for 45 minutes. 517 mg (1.282 mmol) (oxodiperoxy(pyridine) (1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidone)molybdenum(IV)) were added portionwise at −70° C. The mixture was stirred at −70° C. for 1 hour and then allowed to warm to 0° C. After 1 hour at 0° C., the mixture was quenched with 2.5 ml of a saturated solution of sodium sulfite. Water and ethyl acetate were added. The aqueous layer was extracted once with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and concentrated in vacuo. The crude oil was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%) to provide 82 mg (51%) of the title compound as a light brown oil. MS (m/e): 251.1 (MH+).

1. temperaturecooled to −70° C
2. stirringThe brown solution was stirred at −70° C. for 45 minutes
3. stirringThe mixture was stirred at −70° C. for 1 hour
4. temperatureto warm to 0° C
5. waitAfter 1 hour at 0° C.
6. customthe mixture was quenched with 2.5 ml of a saturated solution of sodium sulfite
7. additionWater and ethyl acetate were added
8. extractionThe aqueous layer was extracted once with ethyl acetate
9. dry with materialThe combined organic layers were dried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated in vacuo
12. customThe crude oil was purified on silica gel (Eluent: Heptane/ethyl acetate 0 to 100%)

ORD record

ord-2f1137fb8d3a4b3aae0eedea49f623d6

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09067911B2