2-(4-Benzyloxy-2,6-dichloro-benzyl)-2-aza-spiro[4.5]decan-1-one → 2-(2,6-Dichloro-4-hydroxy-benzyl)-2-aza-spiro[4.5]decan-1-one

HRID 2427470Notes

Reaction equation

HRID 2427470 reaction equation
C([O:8][C:9]1[CH:26]=[C:25]([Cl:27])[C:12]([CH2:13][N:14]2[CH2:18][CH2:17][C:16]3([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)[C:15]2=[O:24])=[C:11]([Cl:28])[CH:10]=1)C1C=CC=CC=1>C(OCC)(=O)C.[OH-].[Pd+2].[OH-]>[Cl:28][C:11]1[CH:10]=[C:9]([OH:8])[CH:26]=[C:25]([Cl:27])[C:12]=1[CH2:13][N:14]1[CH2:18][CH2:17][C:16]2([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]2)[C:15]1=[O:24]

Participants

4

Reactant 1

HCID 671483482-(4-Benzyloxy-2,6-dichloro-benzyl)-2-aza-spiro[4.5]decan-1-one

Product 1

HCID 671480262-(2,6-Dichloro-4-hydroxy-benzyl)-2-aza-spiro[4.5]decan-1-one

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Purge with N2 and H2 a mixture of 2-(4-benzyloxy-2,6-dichloro-benzyl)-2-aza-spiro[4.5]decan-1-one (1.18 g, 2.82 mmol) and 20% palladium (II) hydroxide on carbon (0.50 g) in ethyl acetate (100 mL) and stir under a balloon of H2 for 4 hours at room temperature. Add sodium sulfate to the mixture and filter through hyflo. Remove the solvent in vacuo and purify the crude product on silica isocratically with 9:1 chloroform:methyl t-butyl ether on silica gel to affort 0.72 g (78%) of the titled product. Rf=0.18 (9:1 chloroform:methyl t-butyl ether).

Workup

  1. customPurge with N2 and H2
  2. filtrationAdd sodium sulfate to the mixture and filter through hyflo
  3. customRemove the solvent in vacuo
  4. custompurify the crude product on silica isocratically with 9:1 chloroform

Sources & evidence

ORD record
ord-037e029fb0d640069756f43b292ea3c5
Source dataset
uspto-grants-2011_06
Patent number
US07968585B2

Reaction notes

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