1-Benzyl-4-[1-benzyloxy-3-(ethoxycarbonyl)cyclobutan-3-yl]-2-pyrrolidone → 1-Benzyl-4-[3-(ethoxycarbonyl)-1-hydroxycyclobutan-3-yl]-2-pyrrolidone

HRID 1279664Notes

Reaction equation

HRID 1279664 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:16][CH:15]([O:17]CC3C=CC=CC=3)[CH2:14]2)[CH2:10][C:9]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C(O)C.[OH-].[OH-].[Pd+2]>[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2([C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH2:14][CH:15]([OH:17])[CH2:16]2)[CH2:10][C:9]1=[O:30])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 184278281-Benzyl-4-[1-benzyloxy-3-(ethoxycarbonyl)cyclobutan-3-yl]-2-pyrrolidone

Product 1

HCID 184277971-Benzyl-4-[3-(ethoxycarbonyl)-1-hydroxycyclobutan-3-yl]-2-pyrrolidone

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A 524 mg (1.29 mmol) portion of 1-benzyl-4-[1-benzyloxy-3-(ethoxycarbonyl)cyclobutan-3-yl]-2-pyrrolidone (Isomer A) was dissolved in 20 ml of ethanol, and the solution was mixed with 530 mg of palladium hydroxide on carbon catalyst and subjected to 1.5 hours of catalytic reduction under a hydrogen pressure of 5 atmospheres and under irradiation of light. After removal of the catalyst by filtration, the solvent was evaporated and the resulting residue was purified by a silica gel column chromatography (chloroform:methanol=95:5) to give 454 mg (quantitative) of the title compound.

Workup

  1. custompressure of 5 atmospheres and under irradiation of light
  2. customAfter removal of the catalyst
  3. filtrationby filtration
  4. customthe solvent was evaporated
  5. customthe resulting residue was purified by a silica gel column chromatography (chloroform:methanol=95:5)

Sources & evidence

ORD record
ord-5c8710777867472986b0de0073c50fb5
Source dataset
uspto-grants-2002_09
Patent number
US06448266B1

Reaction notes

Loading…