HCID 54414263, compound → HCID 53804284, compound

HRID 1456572Notes

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[C:27]([CH3:28])=[CH:26][CH:25]=[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[C:27]([CH3:28])=[CH:26][CH:25]=[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

2260 mg of (2R,4R)-1-ethoxycarbonyl-4-benzyloxy-2-{2-[6-methyl-2-(2-phenylethyl)phenoxy]ethyl}pyrrolidine [prepared as described in step (a) above] were dissolved in 20 ml of ethanol, and then 300 mg of a 10% w/w palladium-on-carbon catalyst were added to the resulting solution. The resulting mixture was stirred under a hydrogen atmosphere at atmospheric pressure and at 60° C. for 1.5 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 1840 mg (a quantitative yield) 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-0be117d52c8448d8b2188a34986afb51
Source dataset: uspto-grants-1998_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05843983

Reaction notes

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