HCID 10697569, compound → HCID 10836976, compound

HRID 743370Notes

Reaction equation

HRID 743370 reaction equation
C([O:8][C@H:9]1[CH2:13][N:12]([C:14]([O:16][CH2:17][CH3:18])=[O:15])[C@H:11]([CH2:19][CH2:20][O:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[CH2:28][CH2:29][C:30]2[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[C:32]([O:38][CH3:39])[CH:31]=2)[CH2:10]1)C1C=CC=CC=1>C(O)C.[Pd]>[CH2:17]([O:16][C:14]([N:12]1[CH2:13][C@H:9]([OH:8])[CH2:10][C@H:11]1[CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[CH2:28][CH2:29][C:30]1[CH:31]=[C:32]([O:38][CH3:39])[CH:33]=[C:34]([O:36][CH3:37])[CH:35]=1)=[O:15])[CH3:18]

Participants

4

Reactant 1

HCID 10697569HCID 10697569, compound

Product 1

HCID 10836976HCID 10836976, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of 0.951 g of (2R,4R)-4-benzyloxy-1-ethoxycarbonyl-2-(2-{2-[2-(3,5-dimethoxyphenyl)ethyl]phenoxy}ethyl)pyrrolidine and 95 m g of 5% w/w palladium-on-carbon in 6 ml of ethanol was stirred under an atmosphere of hydrogen at 60° C. for 9 hours. At the end of this time, the mixture was cooled, and the catalyst was removed by filtration. The filtrate was then concentrated by distillation under reduced pressure. The resulting oil was purified by column chromatography through silica gel, using a 1:2 by volume mixture of hexane and ethyl acetate as the eluent, to give 0.717 g (yield 91%) of (2R,4R)-1-ethoxycarbonyl-4-hydroxy-2-(2-{2-[2-(3,5-dimethoxyphenyl)ethyl]phenoxy}ethyl)pyrrolidine as a colorless oil.

Workup

  1. temperatureAt the end of this time, the mixture was cooled
  2. customthe catalyst was removed by filtration
  3. concentrationThe filtrate was then concentrated by distillation under reduced pressure
  4. customThe resulting oil was purified by column chromatography through silica gel
  5. additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-10b01ac6b1fa409b8bf2d88d84cc8c0d
Source dataset
uspto-grants-1996_09
Patent number
US05556864

Reaction notes

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