2-Methylaziridine → E-4-(2-methyl-1-aziridinyl)-2-butenoic acid ethyl ester

HRID 583542Notes

Reaction equation

HRID 583542 reaction equation
C[CH2:2][N:3]([CH2:6][CH3:7])[CH2:4][CH3:5].BrC/C=[CH:11]/[C:12]([O:14][CH2:15][CH3:16])=[O:13].CC1CN1>C1COCC1.CCOC(C)=O>[CH2:15]([O:14][C:12](=[O:13])/[CH:11]=[CH:7]/[CH2:6][N:3]1[CH2:2][CH:4]1[CH3:5])[CH3:16]

Participants

6

Reactant 3

HCID 63772-MethylaziridineHCID 8471TriethylamineHCID 5373944Ethyl (E)-4-bromobut-2-enoate

Product 1

HCID 88285506E-4-(2-methyl-1-aziridinyl)-2-butenoic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add 10 mL of NEt3 to a solution of 9.2 mL of ethyl 4-bromocrotonate and 4 mL of 2-methylaziridine in 100 mL of THF. Stir for 60 h, during which time a white precipitate forms. Dilute the reaction mixture with 300 mL of EtOAc and wash with water and then with brine. Dry the organic solution over MgSO4, filter, and concentrate in vacuo to yield 6.7 g of crude product. Purify by flash chromatography (silica gel, 1:4 hexane/EtOAc) to yield 5.2 g of E-4-(2-methyl-1-aziridinyl)-2-butenoic acid ethyl ester.

Workup

  1. washwash with water
  2. dry with materialDry the organic solution over MgSO4
  3. filtrationfilter
  4. concentrationconcentrate in vacuo
  5. customto yield 6.7 g of crude product
  6. customPurify by flash chromatography (silica gel, 1:4 hexane/EtOAc)

Sources & evidence

ORD record
ord-e6cae2f647df41f1a90721635c5d5780
Source dataset
uspto-grants-1999_07
Patent number
US05929236

Reaction notes

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