Benzylamine → Methyl 1-benzylaziridine-2-carboxylate

HRID 1670021Notes

Reaction equation

HRID 1670021 reaction equation
Br[CH:2]([CH2:7]Br)[C:3]([O:5][CH3:6])=[O:4].C([O-])([O-])=O.[K+].[K+].[CH2:15]([NH2:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[CH2:15]([N:22]1[CH2:7][CH:2]1[C:3]([O:5][CH3:6])=[O:4])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7504BenzylamineHCID 11430Potassium CarbonateHCID 95428Methyl 2,3-dibromopropionate

Product 1

HCID 561085Methyl 1-benzylaziridine-2-carboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 2,3-dibromopropionate (92.50 g, 10.0 mmol) and K2CO3 (4.10 g 30.0 mmol) in acetonitrile (30 mL) was added dropwise benzylamine (1.20 mL, 11 mmol). After being stirred at rt for 4 h, and the reaction mixture was quenched with a saturated aqueous NH4Cl solution. The organic material was extracted with EtOAc, the extracts dried over MgSO4, concentrated in vacuo. The residue was purified by column chomatography (EtOAc/Hex 2/1) to give the title compound (1.62 g, 85%).

Workup

  1. customthe reaction mixture was quenched with a saturated aqueous NH4Cl solution
  2. extractionThe organic material was extracted with EtOAc
  3. dry with materialthe extracts dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chomatography (EtOAc/Hex 2/1)

Sources & evidence

ORD record
ord-76632c52cb93432f9eec1ec57abd645c
Source dataset
uspto-grants-2011_08
Patent number
US07989634B2

Reaction notes

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