HCID 11949850, compound → HCID 11950018, compound

HRID 251462Notes

Reaction equation

HRID 251462 reaction equation
C([N:8]1[CH2:33][CH2:32][C:11]2([N:15]=[C:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH2:23][CH2:24][CH2:25][N:26]4[CH2:30][CH2:29][CH2:28][CH:27]4[CH3:31])=[CH:18][CH:17]=3)[O:13][CH2:12]2)[CH2:10][CH2:9]1)C1C=CC=CC=1>C(O)C.[OH-].[Pd+2].[OH-]>[CH3:31][CH:27]1[CH2:28][CH2:29][CH2:30][N:26]1[CH2:25][CH2:24][CH2:23][O:22][C:19]1[CH:18]=[CH:17][C:16]([C:14]2[O:13][CH2:12][C:11]3([CH2:10][CH2:9][NH:8][CH2:33][CH2:32]3)[N:15]=2)=[CH:21][CH:20]=1

Participants

4

Reactant 1

HCID 11949850HCID 11949850, compound

Product 1

HCID 11950018HCID 11950018, compoundYield 125.6%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalyst2×HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

A suspension of 8-benzyl-2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-3-oxa-1,8-diazaspiro[4.5]dec-1-ene 30 (0.22 g, 0.49 mmol) and palladium hydroxide (0.02 g, 10% wt) in ethanol (10 ml) is placed in a Parr apparatus under a hydrogen atmosphere (40 psi) overnight. After this time, palladium hydroxide (0.02 g, 10% wt) is added again, and the mixture is stirred further under hydrogen at 50° C. for 2 days. The mixture is then filtered on celite and the filtrate is concentrated under reduced pressure to give 0.22 g of 2-{4-[3-(2-methylpyrrolidin-1-yl)propoxy]phenyl}-3-oxa-1,8-diazaspiro[4.5]dec-1-ene 36 as a paste.

Workup

  1. custom(40 psi) overnight
  2. filtrationThe mixture is then filtered on celite
  3. concentrationthe filtrate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-ffb86315d0d7448e9c56ac2384872f96
Source dataset
uspto-grants-2011_01
Patent number
US07863450B2

Reaction notes

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