Ethyl Acetate → 1-cyclopentyl N-[3-(bromomethyl)benzyl]-2-methylalaninate

HRID 632577

반응식

HRID 632577 반응식
[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH:6]=O.[CH:11]1([O:16][C:17](=[O:22])[C:18]([CH3:21])([CH3:20])[NH2:19])[CH2:15][CH2:14][CH2:13][CH2:12]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(OCC)(=O)C>ClC(Cl)C>[Br:1][CH2:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][CH:10]=1)[CH2:6][NH:19][C:18]([CH3:21])([C:17]([O:16][CH:11]1[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:22])[CH3:20]

참가 물질

6

반응물 4

HCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 71278253-(Bromomethyl)benzaldehydeHCID 59622352alpha,alpha-Dimethylglycine cyclopentyl ester

생성물 1

HCID 866864271-cyclopentyl N-[3-(bromomethyl)benzyl]-2-methylalaninate수율 39.2%

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

To a solution of 3-(bromomethyl)-benzaldehyde (0.503 g, 2.52 mmol) in dichloroethane (20 mL) was added α,α-dimethylglycine cyclopentyl ester (0.893 g, 5.2 mmol) and sodium triacetoxyborohydride (1.47 g, 6.9 mmol). The mixture was stirred at room temperature for 3 hours, then poured into ethyl acetate (200 mL) and washed with saturated ammonium chloride solution (3 times 50 mL). The organic fraction was dried (MgSO4), concentrated and purified by flash column chromatography (SiO2, 7:3 heptane:ethyl acetate) to yield the desired product (0.350 g, 39% yield). LC/MS: m/z 354/356 [M+H]+

후처리

  1. washwashed with saturated ammonium chloride solution (3 times 50 mL)
  2. dry with materialThe organic fraction was dried (MgSO4)
  3. concentrationconcentrated
  4. custompurified by flash column chromatography (SiO2, 7:3 heptane:ethyl acetate)

출처 및 근거

ORD 기록
ord-12968c7296d848ee993da33f3dbf7c2e
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321718B2

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