(1S)-1-(2-Iodo-3-methylphenyl)ethanol → (1S)-1-(2-{[6-(4-Fluorophenyl)-2-naphthyl]sulfonyl}-3-methyl-phenyl)ethanol

HRID 735351Notes

Reaction equation

HRID 735351 reaction equation
I[C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=1[C@@H:9]([OH:11])[CH3:10].[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[CH:25]=[C:24]([S:29]([O-:31])=[O:30])[CH:23]=[CH:22]3)=[CH:15][CH:14]=1.[Na+]>>[F:12][C:13]1[CH:18]=[CH:17][C:16]([C:19]2[CH:20]=[C:21]3[C:26](=[CH:27][CH:28]=2)[CH:25]=[C:24]([S:29]([C:2]2[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][C:3]=2[C@@H:9]([OH:11])[CH3:10])(=[O:31])=[O:30])[CH:23]=[CH:22]3)=[CH:15][CH:14]=1

Participants

3

Reactant 2

HCID 10753914(1S)-1-(2-Iodo-3-methylphenyl)ethanolHCID 68900681Sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate

Product 1

HCID 68903161(1S)-1-(2-{[6-(4-Fluorophenyl)-2-naphthyl]sulfonyl}-3-methyl-phenyl)ethanol

Procedure

Prepared according to the method of Example 6 Step 4 using (1S)-1-(2-iodo-3-methylphenyl)ethanol and sodium 6-(4-fluorophenyl)naphthalene-2-sulfinate to give the title compound as a white solid (58 mg). SFC (10% MeOH, chiralpak AD-H) e.e. >99%; 1H NMR (400 MHz, d6-DMSO): δ 8.6 (1H, s), 8.35 (1H, s), 8.31 (1H, d, J=8.7 Hz), 8.17 (1H, d, J=8.7 Hz), 8.03 (1H, d, J=9.4 Hz), 7.93-7.89 (2H, m), 7.85 (1H, d, J=7.7 Hz), 7.75 (1H, m) 7.6 (1H, t, J=8.7 Hz), 7.4-7.35 (2H, t, J=7.5 Hz), 7.3 (1H, d, J=7.4 Hz) 5.9 (1H, m), 5.35 (1H, d, J=7.3 Hz), 2.5 (3H, s) 1.3 (3H, d, J=6.3 Hz); m/z (ES+) 403 [(M-OH)+].

Workup

  1. customPrepared

Sources & evidence

ORD record
ord-f3c514d1e2754211864e2a07b41cb434
Source dataset
uspto-grants-2009_09
Patent number
US07592456B2

Reaction notes

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