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

HRID 2109845ノート

反応式

HRID 2109845 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-05619cf4335748e0b8826f7da7a75642
出典データセット
uspto-grants-2009_04
特許番号
US07517532B2

反応ノート

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