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

HRID 539985Notes

Reaction equation

HRID 539985 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=C(C=CC=1)C(OO)=[O:21].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[CH:13]12[O:21][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 (2.5 g) in dichloromethane (60 mL) was added 3-chloroperoxybenzoic acid (6.08 g, 50-60% purity). The reaction was stirred at room temperature for 72 hours, and then a saturated sodium thiosulfate solution (50 mL) was added. After being stirred for additional 30 minutes, the mixture was extracted with chloroform (50 mL×2). The combined organic layers were washed successively with 2 N aqueous solution of sodium hydroxide (50 mL×2) and brine (50 mL), dried over magnesium sulfate and concentrated in vacuo to afford 2.79 g of the crude benzyl 6-oxa-3-azabicyclo[3.1.0]hexane-3-carboxylate as an oil. MS obsd. (ESI+) [(M+H)+] 220.

Workup

  1. stirringAfter being stirred for additional 30 minutes
  2. extractionthe mixture was extracted with chloroform (50 mL×2)
  3. washThe combined organic layers were washed successively with 2 N aqueous solution of sodium hydroxide (50 mL×2) and brine (50 mL)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9d002bb265c74eeb9a8f074bbc05fccb
Source dataset
uspto-grants-2014_10
Patent number
US08871756B2

Reaction notes

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