HCID 54008280, compound → HCID 53933380, compound

HRID 1870968Notes

Reaction equation

HRID 1870968 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH:13]=[C:12]2[CH2:27][C@H:28]1[CH2:32][CH2:31][CH2:30][N:29]1[CH3:33])C1C=CC=CC=1>C(O)C.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([S:18]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:20])=[O:19])[CH:13]=[C:12]2[CH2:27][C@H:28]1[CH2:32][CH2:31][CH2:30][N:29]1[CH3:33]

Participants

4

Reactant 1

HCID 54008280HCID 54008280, compound

Product 1

HCID 53933380HCID 53933380, compoundYield 93%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of (R)-5-benzyloxy-3-(1-methyl-2-pyrrolidinylmethyl)-1-phenylsulfonylindole (Example 7e, 2.01 g, 4.36 mmol) and 10% Pd/C (0.64 g, 0.436 mmol) in ethanol (25 mL) was stirred under an atmosphere of H2. Filtration to remove the catalyst followed by flash chromatography (silica gel) yielded (R)-5-hydroxy-3-(1-methyl-2-pyrrolidinylmethyl)-1-phenylsulfonylindole (1.5 g, 93%; HRMS-FAB+ : C20H22N2O3S, calculated MH+ :371.14294; found MH+ :371.14081).

Workup

  1. filtrationFiltration
  2. customto remove the catalyst

Sources & evidence

ORD record
ord-6bf17e66d9d44874a01220dc21ee0ed6
Source dataset
uspto-grants-2000_08
Patent number
US06100291

Reaction notes

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