HCID 54022454, compound → HCID 53981935, compound

HRID 1456569Notes

Reaction equation

[CH2:1]([O:3][C:4]([N:6]1[CH2:10][C@H:9]([O:11]CC2C=CC=CC=2)[CH2:8][C@H:7]1[CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1[CH2:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:5])[CH3:2]>C(O)C.[Pd]>[CH2:1]([O:3][C:4]([N:6]1[CH2:10][C@H:9]([OH:11])[CH2:8][C@H:7]1[CH2:19][CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=1[CH2:29][CH2:30][C:31]1[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1)=[O:5])[CH3:2]

Participants

Conditions

Temperature: 60 °C

Procedure

1820 mg of (2R,4R)-1-ethoxycarbonyl-4-benzyloxy-2-{2-[4-methyl-2-(2-phenylethyl)phenoxy]ethyl}pyrrolidine [prepared as described in step (a) above] were dissolved in 20 ml of ethanol, and then 200 mg of a 10% w/w palladium-on-carbon catalyst were added to the resulting solution. The resulting mixture was then stirred under a hydrogen atmosphere at atmospheric pressure and at 60° C. for 2 hours. At the end of this time, the catalyst was removed by filtration, and the reaction mixture was concentrated by evaporation under reduced pressure. The resulting concentrate was purified by silica gel column chromatography, using a 1:2 by volume mixture of hexane and ethyl acetate as the eluent, to give 1410 mg (yield 95%) of the title compound as an oily substance.

Workup

customAt the end of this time, the catalyst was removed by filtration
concentrationthe reaction mixture was concentrated by evaporation under reduced pressure
concentrationThe resulting concentrate
customwas purified by silica gel column chromatography
additionby volume mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record: ord-66c8dae6f7b84167a4e05484ad465ff5
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05843983

Reaction notes

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