Methanol → (2'-Fluoro-4-(hydroxymethyl)-5'-(methyloxy)-1,1'-biphenyl-2-yl)(1-methylcyclopropyl)methanol

HRID 1662534Notes

Reaction equation

HRID 1662534 reaction equation
CC([Si](C)(C)[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([CH:23]([C:25]2([CH3:28])[CH2:27][CH2:26]2)[OH:24])[CH:9]=1)(C)C.CO.CC1C=CC(S([O-])(=O)=O)=CC=1.C1C=C[NH+]=CC=1>CCOC(C)=O>[F:22][C:15]1[CH:16]=[CH:17][C:18]([O:20][CH3:21])=[CH:19][C:14]=1[C:11]1[CH:12]=[CH:13][C:8]([CH2:7][OH:6])=[CH:9][C:10]=1[CH:23]([C:25]1([CH3:28])[CH2:27][CH2:26]1)[OH:24]

Participants

5

Reactant 3

HCID 887MethanolHCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 57706611(4-((((1,1-Dimethylethyl)(dimethyl)silyl)oxy)methyl)-2'-fluoro-5'-(methyloxy)-1,1'-biphenyl-2-yl)(1-methylcyclopropyl)methanol

Product 1

HCID 57706703(2'-Fluoro-4-(hydroxymethyl)-5'-(methyloxy)-1,1'-biphenyl-2-yl)(1-methylcyclopropyl)methanolYield 88%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A 200 mL round bottom flask was charged with 83.18E (0.80 g, 1.9 mmol), MeOH (10 mL), and PPTS (0.047 g, 0.19 mmol). The solution was stirred overnight at room temperature and diluted with EtOAc. The organic phase was washed with water and brine, dried (MgSO4), and concentrated. The crude product was purified by silica gel flash chromatography (20-55% EtOAc/hexane) to afford 83.18F (0.52 g, 88%) as a colorless oil.

Workup

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. customThe crude product was purified by silica gel flash chromatography (20-55% EtOAc/hexane)

Sources & evidence

ORD record
ord-71bef6b37622477a943012288f7d3bfe
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

Loading…