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

HRID 733081Notes

Reaction equation

HRID 733081 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 of Example 1) and K2CO3 (0.51 g, 0.0372 mol) in ethanol-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) in ethanol-H2O (2:1, 150 mL), and the resulting mixture was stirred at the same temperature 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×3). The extracts were dried over Na2SO4, filtered 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 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×3)
  4. dry with materialThe extracts were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. 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-33bcc4ded27a4bb4bf62af3265ffa225
Source dataset
uspto-grants-2009_09
Patent number
US07589109B2

Reaction notes

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