Tert-butyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate → tert-Butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylate

HRID 132333

Reaction equation

HRID 132333 reaction equation
[CH3:1][O:2][C:3](=[O:18])[CH:4]=[C:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:7][CH2:6]1.[H][H]>C(OCC)(=O)C.CO.[Pd]>[CH3:1][O:2][C:3](=[O:18])[CH2:4][CH:5]1[CH2:6][CH2:7][N:8]([C:11]([O:13][C:14]([CH3:16])([CH3:15])[CH3:17])=[O:12])[CH2:9][CH2:10]1

Participants

6

Reactant 2

HCID 10377658Tert-butyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 1514280tert-Butyl 4-(2-methoxy-2-oxoethyl)piperidine-1-carboxylateYield 97%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-Butyl 4-(2-methoxy-2-oxoethylidene)piperidine-1-carboxylate (35.71 g, 140 mmol) was dissolved in a mixture of ethyl acetate (110 mL) and methanol (110 mL). 50% wet 10% palladium on carbon (3.3 g) was added to the mixture. Reaction vessel was charged with 55 psi of hydrogen gas. Reaction shook on a Parr apparatus at room temperature for 16 hours. Reaction mixture was filtered to remove the catalyst. Filtrate was concentrated in vacuo. Title compound was obtained as clear colorless oil in 97% yield. 1H NMR (300 MHz, CDCl3): δ=4.04 (d, J=10.25, 2H), 3.64 (s, 3H), 2.68 (t, J=12.44, 2H), 2.21 (d, J=6.95, 2H), 1.98-1.77 (m, 1H), 1.64 (d, J=13.5, 2H), 1.41 (s, 9H), 1.25-0.99 (m, 2H).

Workup

  1. customReaction vessel
  2. customReaction
  3. customReaction mixture
  4. filtrationwas filtered
  5. customto remove the catalyst
  6. concentrationFiltrate was concentrated in vacuo

Sources & evidence

ORD record
ord-59fecfed641a4de8bcb2b99c951859a3
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Linked notes

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