Benzyl Alcohol → Benzyl 1-benzylaziridine-2-carboxylate

HRID 23887

반응식

HRID 23887 반응식
Br[CH:2]([CH2:6]Br)[C:3](Cl)=[O:4].[CH2:8]([OH:15])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:16]([NH2:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1.C(Cl)Cl>[CH2:16]([N:23]1[CH2:6][CH:2]1[C:3]([O:15][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:4])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

참가 물질

6

반응물 3

HCID 244Benzyl AlcoholHCID 7504BenzylamineHCID 867902,3-Dibromopropanoyl chloride

생성물 1

HCID 86587090Benzyl 1-benzylaziridine-2-carboxylate수율 44%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of 2,3-dibromopropionyl chloride (5.00 g, 19.97 mmol) in THF (25 ml) at 0° C. was added dropwise benzyl alcohol (2.10 ml, 19.97 mmol). After stirring for 1 h, the reaction was concentrated in vacuo and the resulting oil dissolved in CH2Cl2 (25 ml) and treated with a solution of benzyl amine (2.20 ml, 19.97 mmol) and TEA (5.80 ml, 41.94 mmol) in CH2Cl2 (10 ml) at 0° C. After stirring for 3 h, the reaction was filtered and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluted with hexane/ethyl acetate (4:1) to afford N-benzyl-aziridine-2-carboxylic acid, benzyl ester as a colorless oil (2.35 g).

후처리

  1. concentrationthe reaction was concentrated in vacuo
  2. dissolutionthe resulting oil dissolved in CH2Cl2 (25 ml)
  3. stirringAfter stirring for 3 h
  4. filtrationthe reaction was filtered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel
  7. washeluted with hexane/ethyl acetate (4:1)

출처 및 근거

ORD 기록
ord-a9b3277e1a1d4138a3507c1a34129fe5
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855708B2

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