HCID 67436943, compound → HCID 67437067, compound

HRID 351018Notes

Reaction equation

HRID 351018 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]1[S:14]([C:17]1[CH:22]=[CH:21][C:20]([O:23]CC2C=CC=CC=2)=[CH:19][CH:18]=1)(=[O:16])=[O:15])=[O:4]>C(O)C.[Pd]>[CH3:1][O:2][C:3]([C@H:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[N:6]1[S:14]([C:17]1[CH:18]=[CH:19][C:20]([OH:23])=[CH:21][CH:22]=1)(=[O:16])=[O:15])=[O:4]

Participants

4

Reactant 1

HCID 67436943HCID 67436943, compound

Product 1

HCID 67437067HCID 67437067, compoundYield 55.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of the title B compound, (R)-1-(4-benzyloxy-benzenesulfonyl)-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester (3.00 g, 7.1 mmol) in ethanol (200 mL) under nitrogen is added 10% palladium on carbon (0.3 g). The resulting mixture is hydrogenated at 46 psi for 18.5 hours at room temperature. The mixture is filtered through celite by vacuum filtration. The filtrate is concentrated in vacuo to give 1.31 g of (R)-1-(4-hydroxy-benzene-sulfonyl)-2,3-dihydro-1H-indole-2-carboxylic acid methyl ester which is used without further purification: [M+1]+=334.22, [M−1]−=332.16.

Workup

  1. filtrationThe mixture is filtered through celite by vacuum filtration
  2. concentrationThe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-f6fc062a228c408b9c251e9ec8571881
Source dataset
uspto-grants-2007_02
Patent number
US07183304B2

Reaction notes

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