Aziridine → HCID 9855625, compound

HRID 1026529Notes

Reaction equation

HRID 1026529 reaction equation
[NH:1]1[CH2:3][CH2:2]1.C(=O)([O-])[O-].[K+].[K+].Cl[C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]>C(OCC)C>[C:11]([N:1]1[CH2:3][CH2:2]1)([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12]

Participants

5

Reactant 3

HCID 9033AziridineHCID 10387Benzyl chloroformateHCID 11430Potassium Carbonate

Product 1

HCID 9855625HCID 9855625, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a stirred, distilled aziridine solution (500 mL, 0.1 mol) in a round-bottom flask cooling with an ice bath, three equivalents of potassium carbonate was added. After all of the solid dissolved, benzyl chloroformate (1.5 equivalents) in ethyl ether (150 mL) was added over 2 h. The solution was stirred overnight and warmed to room temperature, and the aqueous phase was extracted with methylene chloride (5×30 mL). The organic phases were combined and passed through a flash silica gel pad and concentrated to afford the Cbz-aziridine as colorless thick oil, yield: 7.2 g, 81%.

Workup

  1. temperaturecooling with an ice bath
  2. dissolutionAfter all of the solid dissolved
  3. extractionthe aqueous phase was extracted with methylene chloride (5×30 mL)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-dcb2d924c5d84165a5036084964246f6
Source dataset
uspto-grants-2014_05
Patent number
US08729258B2

Reaction notes

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