Methyl morpholine oxide → 3-(4-Isobutyl-3-(trifluoromethyl)phenyl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde

HRID 1506369Notes

Reaction equation

HRID 1506369 reaction equation
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]3[C:16]4[C:21]([CH2:22][CH2:23][C:12]=23)=[CH:20][C:19]([CH:24]=C)=[CH:18][CH:17]=4)=[CH:7][C:6]=1[C:26]([F:29])([F:28])[F:27])[CH:2]([CH3:4])[CH3:3].C[N+]1([O-])CC[O:34]CC1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.O.[Os](=O)(=O)(=O)=O>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]3[C:16]4[C:21]([CH2:22][CH2:23][C:12]=23)=[CH:20][C:19]([CH:24]=[O:34])=[CH:18][CH:17]=4)=[CH:7][C:6]=1[C:26]([F:29])([F:28])[F:27])[CH:2]([CH3:4])[CH3:3]

Participants

7

Reactant 3

HCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 671691843-(4-Isobutyl-3-(trifluoromethyl)phenyl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole

Product 1

HCID 866698863-(4-Isobutyl-3-(trifluoromethyl)phenyl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehydeYield 100%

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 3-(4-isobutyl-3-(trifluoromethyl)phenyl)-7-vinyl-4,5-dihydronaphtho[1,2-c]isoxazole (Preparation 23C, 0.3 g, 0.755 mmol) in THF (2 mL) was sequentially added N-methylmorpholine N-oxide (50% in water) (0.35 mL, 0.755 mmol) and osmium tetroxide (4% in water) (0.118 mL, 0.015 mmol) at room temperature. The reaction mixture was stirred at room temperature for 60 h. Next, sodium periodate (0.242 g, 1.132 mmol) dissolved in 1.5 mL of water was added at room temperature. The heterogeneous reaction mixture was stirred at room temperature for 30 min. and the reaction mixture was partitioned between ethyl acetate (10 mL) and brine (5 mL). The ethyl acetate layer was dried over sodium sulfate and concentrated to yield 3-(4-isobutyl-3-(trifluoromethyl)phenyl)-4,5-dihydronaphtho[1,2-c]isoxazole-7-carbaldehyde (0.3 g, 0.751 mmol, 100% yield) as an off-white solid. LC/MS M+1=400.2.

Workup

  1. customat room temperature
  2. additionwas added at room temperature
  3. stirringThe heterogeneous reaction mixture was stirred at room temperature for 30 min.
  4. customthe reaction mixture was partitioned between ethyl acetate (10 mL) and brine (5 mL)
  5. dry with materialThe ethyl acetate layer was dried over sodium sulfate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ab929edf82914f8e95e146550d59f65d
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

Loading…