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

HRID 1279650Notes

Reaction equation

HRID 1279650 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([C:13]2([NH:25][C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:16][CH:15]([O:17]CC3C=CC=CC=3)[CH2:14]2)[CH2:10][C:9]1=[O:33])[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([NH:25][C:26]([O:28][C:29]([CH3:31])([CH3:30])[CH3:32])=[O:27])[CH2:16][CH:15]([OH:17])[CH2:14]2)[CH2:10][C:9]1=[O:33])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 184278061-Benzyl-4-[1-benzyloxy-3-(tert-butoxycarbonylamino)cyclobutan-3-yl]-2-pyrrolidone

Product 1

HCID 184278241-Benzyl-4-[3-(tert-butoxycarbonylamino)-1-hydroxycyclobutan-3-yl]-2-pyrrolidone

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A 4.86 g (10.8 mmol) portion of 1-benzyl-4-[1-benzyloxy-3-(tert-butoxycarbonylamino)cyclobutan-3-yl]-2-pyrrolidone (Isomer B) was dissolved in 140 ml of ethanol, and the solution was mixed with 1 g of palladium hydroxide on carbon catalyst and subjected to 1 hour of catalytic reduction under a hydrogen pressure of 3 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 to give 4.01 g (quantitative) of the title compound. Thereafter, optical resolution of Isomers B1 and B2 as enantiomers originated from the pyrrolidine 4 position asymmetric carbon atom of the thus obtained compound was carried out by HPLC under the following conditions.

Workup

  1. custompressure of 3 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

Sources & evidence

ORD record
ord-3db851c5110c4c179c98c97c698e83eb
Source dataset
uspto-grants-2002_09
Patent number
US06448266B1

Reaction notes

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