Methyl morpholine oxide → HCID 68888983, compound

HRID 1820998Notes

Reaction equation

HRID 1820998 reaction equation
[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]=[CH2:23])=[CH:18][C:17]=3[CH3:24])[N:12]=2)=[CH:7][C:6]=1[C:25]([F:28])([F:27])[F:26])([CH3:3])[CH3:2].C[N+]1([O-])CCOCC1.C1COCC1.[OH2:42].[Cl-].[Na+].[OH2:45]>[Os](=O)(=O)(=O)=O>[CH:1]([O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([C:16]3[CH:21]=[CH:20][C:19]([CH:22]([OH:45])[CH2:23][OH:42])=[CH:18][C:17]=3[CH3:24])[N:12]=2)=[CH:7][C:6]=1[C:25]([F:26])([F:27])[F:28])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 82029Methyl morpholine oxideHCID 21881883Oxolane--water (1/1)HCID 57417360Sodium chloride; waterHCID 68891670HCID 68891670, compound

Product 1

HCID 68888983HCID 68888983, compound

Reagents, catalysts & solvents 1

HCID 30318Osmium TetroxideCatalyst

Procedure

To a solution of 215 mg (0.55 mmol) of 5-(4-isopropoxy-3-(trifluoromethyl)phenyl)-3-(2-methyl-4-vinylphenyl)-1,2,4-oxadiazole and 78 mg (0.66 mmol) of 4-methylmorpholine N-oxide in 12 mL of 3:1 v:v THF/H2O mix solvent was added 347 μL (0.03 mmol) osmium tetraoxide (2.5 wt %). After stirring at rt overnight, the mixture was poured into brine and extracted with EtOAc (3×20 mL). Organic layers were combined, dried over Na2SO4, and concentrated. Chromatography on Biotage 40S cartridge using 7:3 v/v EtOAc/hexanes as the eluant afforded 143 mg of the title compound: 1H NMR (500 MHz, CDCl3) δ 1.43 (d, J=5.9, 6H), 2.30 (br. s, 2H), 2.67 (s, 3H), 3.68 (dd, J=8.1, 11.4, 1H), 3.80 (dd, J=3.6, 11.3, 1H), 4.78 (m, 1H), 4.86 (dd, J=3.5, 8.0, 1H), 7.13 (d, J=8.7, 1H), 7.32-7.34 (m, 2H), 8.05 (d, J=8.0, 1H), 8.29 (dd, J=2.2, 8.8, 1H), 8.41 (d, J=2.1, 1H).

Workup

  1. extractionextracted with EtOAc (3×20 mL)
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-5e9729a2e91548deb8e5317cbad53e8b
Source dataset
uspto-grants-2009_10
Patent number
US07605171B2

Reaction notes

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