Methyl morpholine oxide → HCID 21099390, compound

HRID 2376992Notes

Reaction equation

HRID 2376992 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C@@H:25]([OH:27])[CH3:26])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.C[N+]1([O-])CCOCC1>[Ru]([O-])(=O)(=O)=O.C([N+](CCC)(CCC)CCC)CC.C(Cl)Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5](/[CH:8]=[CH:9]/[C:10]2[CH:15]=[CH:14][C:13]([S:16]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3[C:25](=[O:27])[CH3:26])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 82029Methyl morpholine oxideHCID 11545423HCID 11545423, compound

Product 1

HCID 21099390HCID 21099390, compoundYield 84.9%

Reagents, catalysts & solvents 2

HCID 178419074HCID 178419074, compoundCatalystHCID 6344DichloromethaneSolvent

Procedure

(1S)-1-[2-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]ethanol (Example 135; 100 mg, 0.26 mmol), N-methylmorpholine-N-oxide (46 mg, 0.39 mmol), 4 Å activated molecular sieves (100 mg) and CH2Cl2 (2.6 mL) were combined under N2 and stirred for 20 minutes prior to addition of tetra(n-propyl)ammonium perruthenate (4.6 mg, 0.013 mmol). After a further 20 minutes, the mixture purified by flash chromatography (eluant 40% EtOAc/isohexane) to afford 1-[2-({4-[(E)-2-(4-fluorophenyl)vinyl]phenyl}sulfonyl)phenyl]ethanone as a white solid (84 mg). δH (400 MHz, d6 DMSO): 8.10 (1H, d, J 7.8), 7.88 (2H, d, J 8.5), 7.80 (3H, dd, J 0.0, 8.7), 7.72-7.68 (3H, m), 7.62 (1H, d, J 6.6), 7.46 (1H, d, J 16.5), 7.32-7.22 (3H, m), 2.61 (3H, s). m/z (ES+) 380 [MH+].

Workup

  1. waitAfter a further 20 minutes
  2. customthe mixture purified by flash chromatography (eluant 40% EtOAc/isohexane)

Sources & evidence

ORD record
ord-d43a1fb1a89846fca5acd9f2da11543c
Source dataset
uspto-grants-2008_12
Patent number
US07468393B2

Reaction notes

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