Sodium Carbonate → tert-Butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylate

HRID 1480529Notes

Reaction equation

HRID 1480529 reaction equation
C([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10]([CH3:16])([CH3:15])[CH2:9]1)C1C=CC=CC=1.[C:17](=[O:28])([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])OC(C)(C)C.C(=O)([O-])[O-].[Na+].[Na+]>C(OCC)(=O)C.C(O)C.[Pd]>[C:17]([N:8]1[CH2:13][CH2:12][C:11](=[O:14])[C:10]([CH3:16])([CH3:15])[CH2:9]1)([O:23][C:24]([CH3:25])([CH3:26])[CH3:27])=[O:28]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 97944131-Benzyl-3,3-dimethylpiperidin-4-oneHCID 10219638Carbonic acid, bis(1,1-dimethylethyl) ester

Product 1

HCID 22278899tert-Butyl 3,3-dimethyl-4-oxopiperidine-1-carboxylateYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

To a solution of 1-benzyl-3,3-dimethylpiperidin-4-one (0.217 g, 1.00 mmol, 1.0 eq) in ethyl acetate-ethanol (1:1, 10 mL) was added palladium on carbon (approximately 0.100 g). The reaction was purged with nitrogen followed by hydrogen and stirred under an atmosphere of hydrogen for 1 hour. The reaction was purged with nitrogen and di-tert-butyl carbonate (0.327 g, 1.50 mmol, 1.5 eq) and sodium carbonate (0.212 g, 2.00 mmol, 2.0 eq) were added. The solution was stirred at room temperature for 1.5 hours and the reaction filtered through Celite®, eluting with EtOAc (4×20 mL). The filtrate was concentrated under reduced pressure. MPLC (15→50% EtOAc-hexane) yielded the title compound (0.206 g, 91%) as a white solid; 1H nmr (CDCl3) δ 3.69 (2H, dd, J 6.5, 6.0 Hz, pipH-6), 3.40 (2H, s, pipH-2), 2.46 (2H, t, J 6.5 Hz, pipH-5), 1.46 (9H, s, C(CH3)3), 1.08 (6H, s, 2×CH3); 13C nmr (CDCl3) δ 177.2, 154.7, 80.1, 54.9, 46.5, 43.4, 37.6, 28.3, 22.4; m/z 172 [M+H—C4H8]+.

Workup

  1. customThe reaction was purged with nitrogen
  2. additionwere added
  3. stirringThe solution was stirred at room temperature for 1.5 hours
  4. filtrationthe reaction filtered through Celite®
  5. washeluting with EtOAc (4×20 mL)
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-46cac0d4072e4edfa393f406686493e0
Source dataset
uspto-grants-2016_08
Patent number
US09409884B2

Reaction notes

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