Diethyl Ether → 2-Benzyloxycarbonyl-3-azabicyclo(3.1.0)hex-2-ene
Reaction equation
ClO[C:3]([CH3:6])([CH3:5])[CH3:4].[C:7]([CH:10]1[NH:15][CH2:14][CH:13]2[CH:11]1[CH2:12]2)([OH:9])=[O:8].C(N([CH2:21][CH3:22])CC)C.[CH2:23](OCC)C>>[CH2:4]([O:8][C:7]([C:10]1[CH:11]2[CH:13]([CH2:14][N:15]=1)[CH2:12]2)=[O:9])[C:3]1[CH:6]=[CH:22][CH:21]=[CH:23][CH:5]=1Participants
Procedure
1.84 g of tert-butyl hypochlorite was added dropwise to a solution of 3.69 g of the benzyl ester of 2-carboxy-3-azabicyclo(3.1.0)-hexane, containing 84% of trans isomer, in 70 ml of dry diethyl ether at 0° to 5° C. under nitrogen. The solution was stirred at 0° to 5° C., in the dark, for 15 minutes, then 5 ml of freshly-distilled triethylamine was added. The suspension was stirred at room temperature for 2 days, and was then concentrated by evaporation. The residue was shaken with 500 ml of diethyl ether and 25 ml of water, and the ether layer was separated, washed with 25 ml of water, dried over sodium sulfate and the solvent was evaporated. The residue was purified chromatographically to give 2.3 g of 2-benzyloxycarbonyl-3-azabicyclo(3.1.0)hex-2-ene. The identity of the product was confirmed by elemental analysis and IR spectrum analysis.
Workup
- additioncontaining 84% of trans isomer
- customat 0° to 5° C.
- stirringThe suspension was stirred at room temperature for 2 days
- concentrationwas then concentrated by evaporation
- stirringThe residue was shaken with 500 ml of diethyl ether and 25 ml of water
- customthe ether layer was separated
- washwashed with 25 ml of water
- dry with materialdried over sodium sulfate
- customthe solvent was evaporated
- customThe residue was purified chromatographically
Sources & evidence
- ORD record
- ord-b819cf963b764cd78b44de3a845b79fc
- Source dataset
- uspto-grants-1981_02
- Patent number
- US04249936
Reaction notes
Loading…