Citric Acid → Benzyl 2-methylaziridine-1-carboxylate

HRID 255457

Reaction equation

HRID 255457 reaction equation
[CH3:1][CH:2]1[CH2:4][NH:3]1.C(N(CC)CC)C.[CH2:12]([O:19][C:20](Cl)=[O:21])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(Cl)Cl>[C:20]([N:3]1[CH2:4][CH:2]1[CH3:1])([O:19][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[O:21]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 63772-MethylaziridineHCID 8471TriethylamineHCID 10387Benzyl chloroformate

Product 1

HCID 21895246Benzyl 2-methylaziridine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Methyl aziridine is dissolved in CH2Cl2 and triethylamine under argon at 0° C. Benzylchloroformate is added and the contents of the flask are at room temperature overnight. The mixture is poured into 10% citric acid and is 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-methyl aziridine.

Workup

  1. customat 0° C
  2. extractionis extracted 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-1a4e7089217245829b297700e2f626b8
Source dataset
uspto-grants-1987_10
Patent number
US04698231

Linked notes

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