Benzyl Bromide → Ethyl 2-((benzyl(cyclopentyl)amino)methyl)-2-hydroxybutanoate

HRID 914162노트

반응식

HRID 914162 반응식
[CH:1]1([NH:6][CH2:7][C:8]([OH:16])([CH2:14][CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:17](Br)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>C(#N)C>[CH2:17]([N:6]([CH2:7][C:8]([OH:16])([CH2:14][CH3:15])[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:1]1[CH2:2][CH2:3][CH2:4][CH2:5]1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

참가 물질

6

반응물 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 57955553Ethyl 2-((cyclopentylamino)methyl)-2-hydroxybutanoate

생성물 1

HCID 57955651Ethyl 2-((benzyl(cyclopentyl)amino)methyl)-2-hydroxybutanoate수율 77%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
80 °C

실험 절차

To ethyl 2-((cyclopentylamino)methyl)-2-hydroxybutanoate (2.7 g, 12 mmol) in 50 ml of acetonitrile at room temperature, was added benzyl bromide (2.1 ml, 18 mmol) dropwise, followed by K2CO3 (5 g, 35 mmol). The reaction mixture was heated at 80° C. for 18 h. It was then diluted to EtOAc, washed by brine and water. Organic extract dried and concentrated to a residue, which was purified on silica gel column chromatographically (Hex/EtOAc=100:1 to 4:1) to give 2.9 g product (77%). [M+H] calc'd for C19H29NO3, 320. found 320.

후처리

  1. washwashed by brine and water
  2. extractionOrganic extract
  3. customdried
  4. concentrationconcentrated to a residue, which
  5. customwas purified on silica gel column chromatographically (Hex/EtOAc=100:1 to 4:1)

출처 및 근거

ORD 기록
ord-0d15590e959a43d39dae2870566636f9
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08026234B2

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