Citric Acid → N-Cbz-2,2-dimethylaziridine

HRID 255462Notes

Reaction equation

HRID 255462 reaction equation
[CH3:1][C:2]1([CH3:5])[CH2:4][NH:3]1.C(N(CC)CC)C.[CH2:13]([O:20][C:21](Cl)=[O:22])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[C:21]([N:3]1[CH2:4][C:2]1([CH3:5])[CH3:1])([O:20][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:22]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 8471TriethylamineHCID 10387Benzyl chloroformateHCID 2272442,2-Dimethylaziridine

Product 1

HCID 13930700N-Cbz-2,2-dimethylaziridine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,2-Dimethyl aziridine is dissolved in CH2Cl2 and triethyamine under argon at 0° C. Benzylchloroformate is added and the contents of the flask are stirred at room temperature overnight. The mixture is poured into 10% citric acid and extracted with CHCl3. The organic layer is washed with dilute aqueous NaHCO3 and dried over MgSO4. The solution is evaporated to yield N-Cbz-2,2-dimethylaziridine.

Workup

  1. customat 0° C
  2. extractionextracted with CHCl3
  3. washThe organic layer is washed with dilute aqueous NaHCO3
  4. dry with materialdried over MgSO4
  5. customThe solution is evaporated

Sources & evidence

ORD record
ord-aec8a86f4aac4f3c83321cc82ef0789e
Source dataset
uspto-grants-1987_10
Patent number
US04698231

Reaction notes

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