Benzyl 3-methyl-2-oxo-2,2',3,3'-tetrahydro-1H,1'H-spiro[1,8-naphthyridine-4,4'-pyridine]-1'-carboxylate → 3-Methyl-1H-spiro[1,8-naphthyridine-4,4'-piperidin]

HRID 1664804Notes

Reaction equation

HRID 1664804 reaction equation
[CH3:1][CH:2]1[C:11]2([CH:16]=[CH:15][N:14](C(OCC3C=CC=CC=3)=O)[CH2:13][CH2:12]2)[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][C:3]1=O>C(O)C.[Pd]>[CH3:1][C:2]1[C:11]2([CH2:16][CH2:15][NH:14][CH2:13][CH2:12]2)[C:10]2[C:5](=[N:6][CH:7]=[CH:8][CH:9]=2)[NH:4][CH:3]=1

Participants

4

Reactant 1

HCID 67440213Benzyl 3-methyl-2-oxo-2,2',3,3'-tetrahydro-1H,1'H-spiro[1,8-naphthyridine-4,4'-pyridine]-1'-carboxylate

Product 1

HCID 866201203-Methyl-1H-spiro[1,8-naphthyridine-4,4'-piperidin]

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Benzyl 3-methyl-2-oxo-2,2′,3,3′-tetrahydro-1H,1′H-spiro[1,8-naphthyridine-4,4′-pyridine]-1′-carboxylate (73 mg, 0.20 mmol) was diluted in ethanol (10 mL) and palladium (10% on carbon; 100 mg) was added. The reaction vessel was evacuated and back-filled with nitrogen (3×), then back-filled with hydrogen (1 atm). After 6 h, the mixture was filtered with celite, washed with ethanol and methanol. The filtrate was concentrated to give the title compound. MS 232.1 (M+1).

Workup

  1. customThe reaction vessel was evacuated
  2. additionback-filled with nitrogen (3×)
  3. additionback-filled with hydrogen (1 atm)
  4. filtrationthe mixture was filtered with celite
  5. washwashed with ethanol and methanol
  6. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-b08268ab758448fa835e83b2334c30f1
Source dataset
uspto-grants-2011_10
Patent number
US08039460B2

Reaction notes

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