Methyl morpholine oxide → Methyl 7-formyl-4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylate

HRID 1506391Notes

Reaction equation

HRID 1506391 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[C:12]1[O:11][N:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[C:8]=1[CH2:7][CH2:6]2)=C.C[N+]1([O-])CC[O:24]CC1.I([O-])(=O)(=O)=O.[Na+]>C1COCC1.[Os](=O)(=O)(=O)=O.O>[CH:1]([C:3]1[CH:4]=[C:5]2[C:13](=[CH:14][CH:15]=1)[C:12]1[O:11][N:10]=[C:9]([C:16]([O:18][CH3:19])=[O:17])[C:8]=1[CH2:7][CH2:6]2)=[O:24]

Participants

8

Reactant 3

HCID 82029Methyl morpholine oxideHCID 23667635Sodium periodateHCID 68182163Methyl 7-vinyl-4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylate

Product 1

HCID 86669891Methyl 7-formyl-4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylate

Reagents, catalysts & solvents 4

HCID 962WaterCatalystHCID 962WaterSolvent3×HCID 8028TetrahydrofuranSolventHCID 30318Osmium TetroxideSolvent

Procedure

To a clear solution of methyl 7-vinyl-4,5-dihydronaphtho[2,1-d]isoxazole-3-carboxylate (Preparation 45B, 65 mg, 0.255 mmol) in THF (4 mL) were sequentially added N-methylmorpholine-N-oxide in water (0.084 mL, 0.407 mmol) and osmium tetroxide in water (0.062 mL, 10.19 μmol) at room temperature. The solution was stirred vigorously at room temperature overnight. Sodium periodate (109 mg, 0.509 mmol) in water (1 mL) was added and the mixture was stirred at room temperature under nitrogen for two hours. Water (2 mL) was then added and the mixture was concentrated to remove THF. The resulting solid was filtered, washed with water (2×2 mL), and dried to give 72 mg of product as a yellow solid. The compound had an HPLC ret. time=0.88/2.0 min. (condition E).

Workup

  1. customat room temperature
  2. stirringthe mixture was stirred at room temperature under nitrogen for two hours
  3. concentrationthe mixture was concentrated
  4. customto remove THF
  5. filtrationThe resulting solid was filtered
  6. washwashed with water (2×2 mL)
  7. customdried

Sources & evidence

ORD record
ord-13d1023f6b47497cb8d04771b130973f
Source dataset
uspto-grants-2015_12
Patent number
US09216972B2

Reaction notes

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