HCID 67422161, compound → HCID 46214029, compound

HRID 880714Notes

Reaction equation

HRID 880714 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([O:19]CC3C=CC=CC=3)=[CH:15][C:14]=2[O:27]CC2C=CC=CC=2)[CH2:9]1)=[O:7])[CH:2]([CH3:4])[CH3:3]>CO.[Pd]>[CH2:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH:10]([C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[OH:27])[CH2:9]1)=[O:7])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 67422161HCID 67422161, compound

Product 1

HCID 46214029HCID 46214029, compoundYield 75%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

In a 25 ml round-bottomed flask, 0.22 g of 3-(2,4-bis(benzyloxy)phenyl)pyrrolidine-1-carboxylic acid isobutyl ester is dissolved in 6 ml of methanol in the presence of 0.1 g of palladium-on-charcoal at 10%. The reaction mixture is stirred for 18 hours under a hydrogen atmosphere. The reaction mixture is filtered and the residue is then chromatographed on silica gel (1/1 heptane/ethyl acetate). 0.1 g of 3-(2,4-dihydroxyphenyl)pyrrolidine-1-carboxylic acid isobutyl ester is obtained. Yield=75%.

Workup

  1. filtrationThe reaction mixture is filtered
  2. customthe residue is then chromatographed on silica gel (1/1 heptane/ethyl acetate)

Sources & evidence

ORD record
ord-9fd10fe5b49e4bbf9ec9ded9653219cb
Source dataset
uspto-grants-2015_03
Patent number
US08993596B2

Reaction notes

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