Water → Tert-butyl 2-acetylmorpholine-4-carboxylate

HRID 2206651Notes

Reaction equation

CON(C)[C:4]([CH:6]1[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]1)=[O:5].[CH3:20][Mg+].[Br-].O>C1COCC1>[C:4]([CH:6]1[O:11][CH2:10][CH2:9][N:8]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:7]1)(=[O:5])[CH3:20]

Participants

Conditions

Temperature: -78 °C

Procedure

To a solution of tert-butyl 2-(methoxy(methyl)carbamoyl)morpholine-4-carboxylate (11 g, 4.0 mmol) in THF (40 mL) was added CH3MgBr (4 mL, 12 mmol) at −78° C. The mixture was stirred at −78° C. for 3 hr. Water (20 mL) was added and the mixture was extracted by ethyl acetate (80 mL*3). The organic layer was washed with brine and dried over sodium sulfate. The crude product was concentrated and purified by column chromatography on silica gel (eluted: petroleum ether/ethyl acetate=10/1) to give tert-butyl 2-acetylmorpholine-4-carboxylate (8 g, 86%).

Workup

extractionthe mixture was extracted by ethyl acetate (80 mL*3)
washThe organic layer was washed with brine
dry with materialdried over sodium sulfate
concentrationThe crude product was concentrated
custompurified by column chromatography on silica gel (eluted: petroleum ether/ethyl acetate=10/1)

Sources & evidence

ORD record: ord-12f4f898b5494ed6b50ae5ed59d47b97
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371331B2

Reaction notes

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