HCID 66700616, compound → HCID 59505470, compound

HRID 1253735Notes

Reaction equation

HRID 1253735 reaction equation
C([N:8]1[CH2:12][CH2:11][C:10]2([CH2:17][CH2:16][C:15]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[CH:14][CH2:13]2)[CH2:9]1)C1C=CC=CC=1>CO.[OH-].[OH-].[Pd+2]>[N:20]1[CH:21]=[CH:22][CH:23]=[C:18]([CH:15]2[CH2:16][CH2:17][C:10]3([CH2:9][NH:8][CH2:12][CH2:11]3)[CH2:13][CH2:14]2)[CH:19]=1

Participants

4

Reactant 1

HCID 66700616HCID 66700616, compound

Product 1

HCID 59505470HCID 59505470, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-benzyl-8-(pyridin-3-yl)-2-azaspiro[4.5]dec-7-ene (250 mg, 0.822 mmol, 1.0 eq.) in MeOH (15 ml) was degassed with argon for 15 min, followed by addition of Pd(OH)2 (125 mg, 50% by wt.). The reaction mixture was stirred under H2 balloon pressure for 4.5 h at RT. After completion of the reaction (monitored by LCMS), the reaction mixture was filtered through celite and the filtrate was concentrated under reduced pressure to yield the desired compound as an off-white solid which was used in the next step without further purification. Yield: 93% (165 mg, 0.76 mmol).

Workup

  1. customAfter completion of the reaction (monitored by LCMS)
  2. filtrationthe reaction mixture was filtered through celite
  3. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-595a060479234bb7b8ea9699cd555613
Source dataset
uspto-grants-2013_06
Patent number
US08455475B2

Reaction notes

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