Ammonium Chloride → 4-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylcyclohexanecarboxamide

HRID 1361841Notes

Reaction equation

[Si:1]([O:8][CH:9]1[CH2:14][CH2:13][CH:12]([C:15]([O:17]CC)=O)[CH2:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.[CH3:21][NH:22][O:23][CH3:24].C([Mg]Cl)(C)C.[Cl-].[NH4+]>C1COCC1.C(OCC)(=O)C>[Si:1]([O:8][CH:9]1[CH2:10][CH2:11][CH:12]([C:15]([N:22]([O:23][CH3:24])[CH3:21])=[O:17])[CH2:13][CH2:14]1)([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

Participants

Conditions

Temperature: 0 °C

Procedure

Ethyl 4-(tert-butyldimethylsilyloxy)cyclohexane-carboxylate (5.73 g, 20.0 mmol) obtained in Step 1 and N,O-dimethylhydroxylamine hydrochloride (2.93 g, 30.0 mmol) were suspended in THF (40 mL), and a 2.0 mol/L solution of isopropylmagnesium chloride in THF (30.0 mL, 60.0 mmol) was added dropwise thereto in a atmosphere of argon at −20° C., followed by stirring at 0° C. for 1 hour. A saturated aqueous solution of ammonium chloride and ethyl acetate were added to the reaction mixture for extraction. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:4) to afford 4-(tert-butyldimethylsilyloxy)-N-methoxy-N-methylcyclo-hexanecarboxamide (6.03 g, 100%).

Workup

customat −20° C.
washThe organic layer was washed with a saturated aqueous solution of sodium chloride
dry with materialdried over anhydrous magnesium sulfate
distillationthe solvent was distilled away under reduced pressure
customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record: ord-7b24f47d48b74c88a25c0ab200af7fe9
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07880013B2

Reaction notes

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