1-Methyl-1,4-cyclohexadiene → HCID 70896057, compound

HRID 2403655Notes

Reaction equation

HRID 2403655 reaction equation
[C:1]12([N:6]3[CH:29]=[C:28]4[C:8]([C:9](=[O:30])[CH2:10][C:11]5([CH2:27]4)[CH2:16][CH2:15][N:14](C(OCC4C=CC=CC=4)=O)[CH2:13][CH2:12]5)=[N:7]3)[CH2:5][CH:3]([CH2:4]1)[CH2:2]2.CC1CC=CCC=1>C(OCC)(=O)C.[Pd]>[C:1]12([N:6]3[CH:29]=[C:28]4[C:8]([C:9](=[O:30])[CH2:10][C:11]5([CH2:27]4)[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]5)=[N:7]3)[CH2:2][CH:3]([CH2:5]1)[CH2:4]2

Participants

5

Reactant 2

HCID 780061-Methyl-1,4-cyclohexadieneHCID 70896126HCID 70896126, compound

Product 1

HCID 70896057HCID 70896057, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of benzyl 2-(bicyclo[1.1.1]pentan-1-yl)-7-oxo-2,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carboxylate (150 mg, 0.37 mmol) in ethyl acetate (10 mL) was added 10% palladium on carbon (1 mg) and 1-methylcyclohexane-1,4-diene (0.1 mL, 0.9 mmol). The reaction was heated to 80° C. and stirred for 2 hours. The reaction was cooled to room temperature and filtered through Celite. The filtrate was concentrated to give the title compound (100 mg, 100%) as an oil. +ESI (M+H) 272.4; 1H NMR (400 MHz, CDCl3, δ): 7.26 (s, 1 H), 2.82 (dd, J=6.63, 4.49 Hz, 4 H), 2.69 (s, 2 H), 2.60 (s, 1 H), 2.56 (s, 2 H), 2.30 (s, 6 H), 1.47-1.55 (m, 4 H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. filtrationfiltered through Celite
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-7692389eaf3d4a7ab5a6351e5b7144ba
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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