Chlorotrimethylsilane → tert-Butyl 4-((trimethylsilyl)oxy)-5,6-dihydropyridine-1(2H)-carboxylate

HRID 451553Notes

Reaction equation

[O:1]=[C:2]1[CH2:7][CH2:6][N:5]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:4][CH2:3]1.[CH3:15][Si:16](Cl)([CH3:18])[CH3:17].C(N(CC)CC)C.C([O-])(O)=O.[Na+]>CN(C=O)C>[C:11]([O:10][C:8]([N:5]1[CH2:4][CH:3]=[C:2]([O:1][Si:16]([CH3:18])([CH3:17])[CH3:15])[CH2:7][CH2:6]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

Conditions

Temperature: 80 °C

Procedure

tert-Butyl 4-oxopiperidine-1-carboxylate (10 g, 48.7 mmol) was dissolved in dry DMF (12.0 mL). Trimethylsilyl chloride (6.35 g, 7.39 mL, 58.4 mmol) and triethylamine (11.8 g, 16.2 mL, 117 mmol) were added under argon and the reaction mixture was stirred at 80° C. for 16 hours. The reaction mixture was cooled to room temperature, saturated NaHCO3 solution was added and the aqueous phase was extracted with ethyl acetate. The combined organic layers were dried over Na2SO4 and the solvent was evaporated. The residue was purified by flash chromatography (1 drop Et3N was added during conditioning of the column) (silica gel, 100 g, 0% to 100% pentane in Et2O, 45 minutes). The title compound was obtained as a colorless liquid (13.2 g, 99%).

Workup

temperatureThe reaction mixture was cooled to room temperature
extractionthe aqueous phase was extracted with ethyl acetate
dry with materialThe combined organic layers were dried over Na2SO4
customthe solvent was evaporated
customThe residue was purified by flash chromatography (1 drop Et3N
additionwas added during conditioning of the column) (silica gel, 100 g, 0% to 100% pentane in Et2O, 45 minutes)

Sources & evidence

ORD record: ord-30a0836bf6fc469d89fd0058a55fe5f9
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08486967B2

Reaction notes

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