(RS)-4-{1-[4-(3-Benzyloxy-phenyl)-butyl]-pyrrolidine-3-sulfonyl}-phenol → (RS)-4-{1-[4-(3-hydroxy-phenyl)-butyl]-pyrrolidine-3-sulfonyl}-phenol

HRID 1280722Notes

Reaction equation

HRID 1280722 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][CH:21]([S:24]([C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)(=[O:26])=[O:25])[CH2:20]2)[CH:12]=[CH:13][CH:14]=1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][C:9]1[CH:10]=[C:11]([CH2:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:23][CH2:22][CH:21]([S:24]([C:27]3[CH:28]=[CH:29][C:30]([OH:33])=[CH:31][CH:32]=3)(=[O:26])=[O:25])[CH2:20]2)[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 18425855(RS)-4-{1-[4-(3-Benzyloxy-phenyl)-butyl]-pyrrolidine-3-sulfonyl}-phenolHCID 178418361HCID 178418361, compound

Product 1

HCID 18425807(RS)-4-{1-[4-(3-hydroxy-phenyl)-butyl]-pyrrolidine-3-sulfonyl}-phenolYield 70.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(RS)-4-{1-[4-(3-Benzyloxy-phenyl)-butyl]-pyrrolidine-3-sulfonyl}-phenol (88.4 mg, 0.2 mmol) and Pd/C (40 mg, 10% Pd on charcoal) in MeOH (5 ml) were refluxed for 2 hours under an atmospheric pressure of hydrogen. The reaction mixture was then cooled to room temperature, the catalyst was filtered and the filtrate was concentrated. The residue was chromatographed over silica gel (CH2Cl2—MeOH, 19:1) to provide (RS)-4-{1-[4-(3-hydroxy-phenyl)-butyl]-pyrrolidine-3-sulfonyl}-phenol (53 mg, 69%) as a light beige solid, MS: m/e=376.3 (M+H+).

Workup

  1. filtrationthe catalyst was filtered
  2. concentrationthe filtrate was concentrated
  3. customThe residue was chromatographed over silica gel (CH2Cl2—MeOH, 19:1)

Sources & evidence

ORD record
ord-e69a3ea2dc3443119765dbbd828d59e3
Source dataset
uspto-grants-2002_09
Patent number
US06451819B2

Reaction notes

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