Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → [2'-Fluoro-5'-methoxy-2-(1-methoxy-cyclopentyl)-biphenyl-4-yl]-methanol

HRID 1662469Notes

Reaction equation

HRID 1662469 reaction equation
C([Si]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[F:24])=[C:12]([C:25]2([O:30][CH3:31])[CH2:29][CH2:28][CH2:27][CH2:26]2)[CH:11]=1)(C)C)(C)(C)C.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CO>[F:24][C:17]1[CH:18]=[CH:19][C:20]([O:22][CH3:23])=[CH:21][C:16]=1[C:13]1[CH:14]=[CH:15][C:10]([CH2:9][OH:8])=[CH:11][C:12]=1[C:25]1([O:30][CH3:31])[CH2:26][CH2:27][CH2:28][CH2:29]1

Participants

4

Reactant 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57706027tert-Butyl-[2'-fluoro-5'-methoxy-2-(1-methoxy-cyclopentyl)-biphenyl-4-ylmethoxy]-dimethyl-silane

Product 1

HCID 57706279[2'-Fluoro-5'-methoxy-2-(1-methoxy-cyclopentyl)-biphenyl-4-yl]-methanolYield 61%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 66.68E (66 mg, 168 μmol) in MeOH, was added PPTS (11 mg, 45 μmol), and the mixture was stirred for 16 hours. Solvent was then removed in vacuo to give a residue which was purified by Combiflash chromatography to give the product as an oil (30 mg, 61%). MS ESI m/e: 331.2 (M+H)+.

Workup

  1. customSolvent was then removed in vacuo
  2. customto give a residue which
  3. customwas purified by Combiflash chromatography

Sources & evidence

ORD record
ord-9b4585d19f014e1692ba0a52fdd9ec29
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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