2-(Benzenesulfonyl)-3-phenyloxaziridine → HCID 117698840, compound

HRID 1778475Notes

Reaction equation

HRID 1778475 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH:16]2[CH2:17][CH:18]([CH2:20][C:21]([O:23][CH3:24])=[O:22])[CH2:19][CH:12]1[CH2:13][O:14][CH2:15]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(S(N2C(C3C=CC=CC=3)O2)(=O)=[O:32])C=CC=CC=1>C1COCC1>[CH2:1]([O:8][C:9]([N:11]1[CH:12]2[CH2:19][CH:18]([CH:20]([OH:32])[C:21]([O:23][CH3:24])=[O:22])[CH2:17][CH:16]1[CH2:15][O:14][CH2:13]2)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 3204052-(Benzenesulfonyl)-3-phenyloxaziridineHCID 117697335HCID 117697335, compound

Product 1

HCID 117698840HCID 117698840, compoundYield 220.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 7-methoxycarbonylmethyl-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound AI) (130 mg, 0.39 mmol) in anhydrous THF at −78° C. was added 1 M NaN(trimethylsilyl)2 in THF (0.43 mL, 0.43 mmol) during a period of 5 mins. Then the mixture was stirred for 20 mins at −78° C. To this solution was added a pre-cooled (−78° C.) solution of 2-(phenylsulfonyl)-3-phenyloxaziridine (153 mg, 0.585 mmol) in THF. The solution was stirred for 30 mins at −78° C. and then quenched by rapid addition of 6N HCl. The mixture was stirred at room temperature for 30 mins and then diluted with dichloromethane. The mixture was washed with water and 5% aqueous sodium bicarbonate. The organic layer was dried over anhydrous sodium sulfate and then concentrated in vacuo. The residue was purified by flash column chromatography to afford 7-(hydroxy-methoxycarbonyl-methyl)-3-oxa-9-aza-bicyclo[3.3.1]nonane-9-carboxylic acid benzyl ester (Compound AJ) (0.30 g, 85%). MS: calc'd (MH+) 350, measured (MH+) 350.

Workup

  1. additionTo this solution was added
  2. stirringThe solution was stirred for 30 mins at −78° C.
  3. customquenched by rapid addition of 6N HCl
  4. stirringThe mixture was stirred at room temperature for 30 mins
  5. additiondiluted with dichloromethane
  6. washThe mixture was washed with water and 5% aqueous sodium bicarbonate
  7. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-7d83bd3ab69849a6be098fa3e6bd7525
Source dataset
uspto-grants-2016_02
Patent number
US09266904B2

Reaction notes

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