Hydrochloric Acid → HCID 58252518, compound

HRID 2403659Notes

Reaction equation

HRID 2403659 reaction equation
[C:1]([N:5]1[C:28]2[C:27](=[O:29])[CH2:26][C:10]3([CH2:15][CH2:14][N:13](C(OCC4C=CC=CC=4)=O)[CH2:12][CH2:11]3)[CH2:9][C:8]=2[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].CC1CC=CCC=1.Cl>C(O)C.[Pd].C(OCC)(=O)C.O1CCOCC1>[C:1]([N:5]1[C:28]2[C:27](=[O:29])[CH2:26][C:10]3([CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)[CH2:9][C:8]=2[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 780061-Methyl-1,4-cyclohexadieneHCID 58252526HCID 58252526, compound

Product 1

HCID 58252518HCID 58252518, compoundYield 110.2%

Reagents, catalysts & solvents 4

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of benzyl 1-tert-butyl-7-oxo-1,4,6,7-tetrahydrospiro[indazole-5,4′-piperidine]-1′-carboxylate (46.6 g, 118 mmol) in ethanol (730 mL) was added to 10% palladium on carbon (9.4 g). To this mixture was added 1-methyl-1,4-cyclohexadiene (90 mL, 769 mmol). The reaction was stirred at reflux for 2 hours. The reaction was cooled to room temperature and filtered through Celite®. The filtrate was concentrated in vacuo to give a gray solid. The solid was dissolved in ethyl acetate (150 mL) and to this solution was added 4 M hydrochloric acid in 1,4-dioxane (35 mL). The resulting precipitate was collected by filtration and dried under vacuum to afford the title compound (34 g, 97%) as a white solid. +ESI (M+H) 262.5; 1H NMR (400 MHz, CD3OD, δ): 7.34 (s, 1 H) 3.12-3.25 (m, 4 H) 2.90 (s, 2 H) 2.66 (s, 2 H) 1.67-1.85 (m, 4 H) 1.62 (s, 9 H).

Workup

  1. temperatureat reflux for 2 hours
  2. filtrationfiltered through Celite®
  3. concentrationThe filtrate was concentrated in vacuo
  4. customto give a gray solid
  5. filtrationThe resulting precipitate was collected by filtration
  6. customdried under vacuum

Sources & evidence

ORD record
ord-aa5b85b52d544e8bbfcb36a2ad47515a
Source dataset
uspto-grants-2014_08
Patent number
US08802688B2

Reaction notes

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