Cyclopropylamine → 4-Bromo-2-cyclopropylaminomethyl-benzoic acid isopropyl ester

HRID 1869960노트

반응식

HRID 1869960 반응식
[CH:1]([O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[CH2:13]Br)([CH3:3])[CH3:2].[CH:16]1([NH2:19])[CH2:18][CH2:17]1>C(#N)C>[CH:1]([O:4][C:5](=[O:15])[C:6]1[CH:11]=[CH:10][C:9]([Br:12])=[CH:8][C:7]=1[CH2:13][NH:19][CH:16]1[CH2:18][CH2:17]1)([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 69828CyclopropylamineHCID 574242524-Bromo-2-bromomethyl-benzoic acid isopropyl ester2회

생성물 1

HCID 574242534-Bromo-2-cyclopropylaminomethyl-benzoic acid isopropyl ester수율 28.1%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

A stirred, cooled (ice bath) solution of 4-bromo-2-bromomethyl-benzoic acid isopropyl ester (Intermediate 118, 5.1 g, 15.17 mmol) in acetonitrile (25 mL) was treated with cyclopropyl amine (2 mL, 28.9 mmol). The reaction mixture was allowed to warm to ambient temperature. After 2 h, the volatiles were evaporated in vacuo, the residue was diluted with water and extracted with diethyl ether (×2). The combined organic phase was dried over anhydrous magnesium sulfate, filtered and evaporated in vacuo to an oil. Flash column chromatography over silica gel (230-400 mesh) using 4-20% ethyl acetate in hexane as the eluent to afforded the title product (1.33 g, 28%).

후처리

  1. customthe volatiles were evaporated in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with diethyl ether (×2)
  4. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to an oil

출처 및 근거

ORD 기록
ord-72dda06c916141a2a04170fa20a9ac9d
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638648B2

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