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

HRID 404380Notes

Reaction equation

HRID 404380 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 20.5 (66 mg, 168 μmol) in MeOH (3 mL), was added PPTS (11 mg, 45 μmol). The resulting mixture was stirred overnight. Solvent was removed in vacuo to give a residue which was purified by CombiFlash® chromatography to give an oil (30 mg, 61%). MS ESI m/e: 331.2 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-5f98bddfc4e44f00a8962a1dcc1f00c4
Source dataset
uspto-grants-2014_06
Patent number
US08748462B2

Reaction notes

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