Acetic Acid → tert-Butyl 4-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)piperidine-1-carboxylate

HRID 132335Notes

Reaction equation

HRID 132335 reaction equation
C[O:2][C:3](=O)[CH:4]([CH:15]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]1)[CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[N+:12]([O-])=O.C(O)(=O)C.[H][H]>C(OCC)(=O)C.CO.[Pd]>[O:2]=[C:3]1[CH:4]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17][CH2:16]2)[CH2:5][C:6]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:12]1

Participants

7

Reactant 3

HCID 176Acetic AcidHCID 59732041Tert-butyl 4-(1-methoxy-3-(2-nitrophenyl)-1-oxopropan-2-yl)piperidine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 59731916tert-Butyl 4-(2-oxo-1,2,3,4-tetrahydroquinolin-3-yl)piperidine-1-carboxylateYield 47%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

tert-butyl 4-(1-methoxy-3-(2-nitrophenyl)-1-oxopropan-2-yl)piperidine-1-carboxylate (660 mg, 1.7 mmol) was dissolved in a mixture of ethyl acetate (15 mL) and methanol (15 mL). Acetic acid (250 μL, 4.4 mmol) was added to the mixture. A catalytic amount of 50% wet 10% palladium on carbon was added to the mixture. Reaction vessel was charged with 15 psi of hydrogen gas. Reaction shook on a Parr apparatus at room temperature for 2 hours. Reaction mixture was filtered to removed the catalyst. Filtrated was concentrated in vacuo. Silica gel chromatography gave the title compound as orange foam in 47% yield. MS m/e (M−H)−=329.1.

Workup

  1. customReaction vessel
  2. customReaction
  3. customReaction mixture
  4. filtrationwas filtered
  5. customto removed the catalyst
  6. filtrationFiltrated
  7. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-68770150d5864d0e86869496f6fc66f6
Source dataset
uspto-grants-2008_06
Patent number
US07384931B2

Reaction notes

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