Sodium Thiosulfate → Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylate

HRID 1929757Notes

Reaction equation

HRID 1929757 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:15][CH:14]=[CH:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=CC=C(C(OO)=[O:24])C=1.S([O-])([O-])(=O)=S.[Na+].[Na+]>C(Cl)Cl>[CH:13]12[O:24][CH:14]1[CH2:15][N:11]([C:9]([O:8][CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)=[O:10])[CH2:12]2

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 643471Benzyl 3-pyrroline-1-carboxylate

Product 1

HCID 22147363Benzyl 6-oxa-3-azabicyclo(3.1.0)hexane-3-carboxylateYield 103.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-benzyloxycarbonyl-3-pyrroline (5.0 g) in methylene chloride (125 mL) was added m-chloroperbezoic acid (12.17 g) and the mixture was stirred at room temperature for 3 days. To the reaction mixture was added an aqueous saturated sodium thiosulfate solution (100 mL) and the mixture was stirred for 30 minutes. The reaction mixture was extracted with chloroform (×2) and the organic layer was washed successively with an aqueous 2N sodium hydroxide solution (1100 mL×2) and a saturated brine, dried over magnesium sulfate and concentrated in vacuo to give benzyl 6-oxa-3-azabicyclo[3,1,0]hexan-3-carboxylate (5.58 g, yield: 100%) as an oil.

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. extractionThe reaction mixture was extracted with chloroform (×2)
  3. washthe organic layer was washed successively with an aqueous 2N sodium hydroxide solution (1100 mL×2)
  4. dry with materiala saturated brine, dried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b2c2feab50544c8b830be3b9dbf79fc8
Source dataset
uspto-grants-2012_05
Patent number
US08188097B2

Reaction notes

Loading…