Potassium Carbonate → tert-butyl 4-[(4-oxopiperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylate

HRID 16577

Reaction equation

HRID 16577 reaction equation
[NH2:1][CH2:2][C:3]1([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.C([O-])([O-])=O.[K+].[K+].[I-].C([N+]1(C)[CH2:30][CH2:29][C:28](=[O:31])[CH2:27][CH2:26]1)C>C(O)C.O>[O:31]=[C:28]1[CH2:29][CH2:30][N:1]([CH2:2][C:3]2([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]2)[CH2:26][CH2:27]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 110975681-Ethyl-1-methyl-4-oxopiperidin-1-ium iodideHCID 67232834Tert-butyl 4-(aminomethyl)oxane-4-carboxylate

Product 1

HCID 67233968tert-butyl 4-[(4-oxopiperidin-1-yl)methyl]tetrahydro-2H-pyran-4-carboxylateYield 98%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent2×

Procedure

To a refluxing mixture of tert-butyl 4-(aminomethyl)tetrahydro-2H-pyran-4-carboxylate (8.00 g, 0.0372 mol, step 2) and K2CO3 (0.51 g, 0.0372 mol) in EtOH-H2O (2:1, 240 mL) was added dropwise 1-ethyl-1-methyl-4-oxopiperidinium iodide (12.0 g, 0.0445 mol, J. Org. Chem. 1995, 60, 4324-4330) in EtOH-H2O (2:1, 150 mL), and the resulting mixture was stirred at the same temperature (reflux) for 1 h. After cooling to room temperature, the solvent was removed in vacuo. The residue was poured into sat. NaHCO3 aq. (200 mL), and the mixture was extracted with CH2Cl2 (200 mL×three times). The extracts were dried over Na2SO4 and concentrated. The residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (3:1 to 2:1) to give 10.77 g (98%) of the title compound as a colorless syrup.

Workup

  1. customthe solvent was removed in vacuo
  2. additionThe residue was poured into sat. NaHCO3 aq. (200 mL)
  3. extractionthe mixture was extracted with CH2Cl2 (200 mL×three times)
  4. dry with materialThe extracts were dried over Na2SO4
  5. concentrationconcentrated
  6. customThe residue was chromatographed on a column of silica gel eluting with hexane/ethyl acetate (3:1 to 2:1)

Sources & evidence

ORD record
ord-c32255638ee1498a846ed360ccafe3af
Source dataset
uspto-grants-2010_06
Patent number
US07737163B2

Linked notes

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