(2,4-Bis-benzyloxy-5-isopropenyl-phenyl)-[5-(4-hydroxy-1-methyl-piperidin-4-yl)-1,3-dihydro-isoindol-2-yl]-methanone → (2,4-Dihydroxy-5-isopropyl-phenyl)-[5-(4-hydroxy-methyl-piperidin-4-yl)-1,3-dihydro-isoindol-2-yl]-methanone

HRID 41473Notes

Reaction equation

HRID 41473 reaction equation
C([O:8][C:9]1[CH:14]=[C:13]([O:15]CC2C=CC=CC=2)[C:12]([C:23]([CH3:25])=[CH2:24])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:37]3([OH:44])[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]3)[CH:34]=2)[CH2:29]1)=[O:27])C1C=CC=CC=1>CO.[Pd]>[OH:8][C:9]1[CH:14]=[C:13]([OH:15])[C:12]([CH:23]([CH3:25])[CH3:24])=[CH:11][C:10]=1[C:26]([N:28]1[CH2:36][C:35]2[C:30](=[CH:31][CH:32]=[C:33]([C:37]3([OH:44])[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]3)[CH:34]=2)[CH2:29]1)=[O:27]

Participants

4

Reactant 1

HCID 46915491(2,4-Bis-benzyloxy-5-isopropenyl-phenyl)-[5-(4-hydroxy-1-methyl-piperidin-4-yl)-1,3-dihydro-isoindol-2-yl]-methanone

Product 1

HCID 11955673(2,4-Dihydroxy-5-isopropyl-phenyl)-[5-(4-hydroxy-methyl-piperidin-4-yl)-1,3-dihydro-isoindol-2-yl]-methanoneYield 101%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(2,4-Bis-benzyloxy-5-isopropenyl-phenyl)-[5-(4-hydroxy-1-methyl-piperidin-4-yl)-1,3-dihydro-isoindol-2-yl]-methanone (Example 50F) (1.62 g, 2.75 mmol) was dissolved in methanol (50 mL) and hydrogenated at 50° C. over 10% palladium on charcoal using an H-cube hydrogenation apparatus, under free hydrogen conditions. Concentration afforded the title compound (1.14 g, 100%) as a yellow solid, the NMR and mass spectrometric data of which were as set out in Example 50E.

Workup

  1. concentrationConcentration

Sources & evidence

ORD record
ord-19267785e3a84716a3f1462ff7764dfb
Source dataset
uspto-grants-2013_09
Patent number
US08530469B2

Reaction notes

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