HCID 178418361, compound → HCID 178515021, compound

HRID 271332Notes

Reaction equation

HRID 271332 reaction equation
[O:1]=[C:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][O:4][C@H:5]1[CH2:10][CH2:9][C@H:8]([N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH2:7][CH2:6]1.[H][H]>[Pd].C(O)C>[OH:1][CH:2]([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[CH2:3][O:4][C@H:5]1[CH2:6][CH2:7][C@H:8]([N:11]2[C:19](=[O:20])[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]2=[O:21])[CH2:9][CH2:10]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178521453HCID 178521453, compound

Product 1

HCID 178515021HCID 178515021, compoundYield 99.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 1 g of trans-2-[4-(2-oxo-2-phenyl-ethoxy)-cyclohexyl]-isoindole-1,3-dione and 0.1 g of 10% palladium on carbon in 100 mL of ethanol was stirred under 1 atm. of hydrogen overnight. The catalyst was filtered off and the filtrate concentrated to dryness under reduced pressure. Drying under vacuum gave 1.0 g of product as a white crystalline solid: 1H NMR (400 MHz, CDCl3) 7.8 (m, 2H), 7.65 (t, 1H), 7.4-7.2 (m, 5H), 4.82 (d, 1H), 4.1 (m, 1H), 3.65 (m, 2H), 3.4 (m, 2H), 2.3 (dd, 2H), 2.2 (m, 2H), 1.8 (d, 2H), 1.4 (dd, 2H).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate concentrated to dryness under reduced pressure
  3. customDrying under vacuum

Sources & evidence

ORD record
ord-2cf9c0f60b1f419481f43cb9f0af1f5a
Source dataset
uspto-grants-2008_11
Patent number
US07452893B2

Reaction notes

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