Ethyl bromoacetate → Methyl {2-[(benzyloxy)methyl]aziridin-1-yl}acetate

HRID 2109845Notes

Reaction equation

HRID 2109845 reaction equation
[CH2:1]([O:8][CH2:9][CH:10]1[CH2:12][NH:11]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)C(C)C)(C)C.Br[CH2:23][C:24]([O:26][CH2:27]C)=[O:25]>ClCCl>[CH2:1]([O:8][CH2:9][CH:10]1[CH2:12][N:11]1[CH2:23][C:24]([O:26][CH3:27])=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 81531DiisopropylethylamineHCID 866027862-[(Benzyloxy)methyl]aziridine

Product 1

HCID 57634653Methyl {2-[(benzyloxy)methyl]aziridin-1-yl}acetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a cold (−78° C.) solution of 2-[(benzyloxy)methyl]aziridine (0.42 g, 2.57 mmol) and N,N-diisopropylethylamine (0.5 mL, 2.90 mmol) in dichloromethane (15 mL) under an atmosphere of nitrogen, ethyl bromoacetate (0.39, 2.5 mmol) was added over a period of 1 h. The resultant mixture was allowed to slowly warm up to room temperature and stirred overnight. The resultant mixture was washed with brine, dried over anhydrous magnesium sulfate, filtered, and concentrated under vacuum. The residue was subjected to column chromatography on silica gel eluting with a mixture of 70% ethyl acetate in hexane. Collection and concentration of appropriate fractions provided the title compound.

Workup

  1. washThe resultant mixture was washed with brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under vacuum
  5. additionThe residue was subjected to column chromatography on silica gel eluting with a mixture of 70% ethyl acetate in hexane
  6. customCollection and concentration of appropriate fractions

Sources & evidence

ORD record
ord-05619cf4335748e0b8826f7da7a75642
Source dataset
uspto-grants-2009_04
Patent number
US07517532B2

Reaction notes

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