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

HRID 632577

Reaktionsgleichung

Reaktionsgleichung von HRID 632577
[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]

Komponenten

6

Edukt 4

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

Produkt 1

HCID 866864271-cyclopentyl N-[3-(bromomethyl)benzyl]-2-methylalaninateAusbeute 39,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

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]+

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-12968c7296d848ee993da33f3dbf7c2e
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321718B2

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