Ethyl Acetate → 1-Cyclopentyl 1-{[3-(bromomethyl)benzyl]amino}cyclopentanecarboxylate

HRID 632578Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 632578
[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:24])[C:18]2([CH2:23][CH2:22][CH2:21][CH2:20]2)[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]1([C:17]([O:16][CH:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)=[O:24])[CH2:20][CH2:21][CH2:22][CH2:23]1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 5049666Sodium triacetoxyborohydrideHCID 71278253-(Bromomethyl)benzaldehydeHCID 581390221-Cyclopentyl 1-aminocyclopentanecarboxylate

Produkt 1

HCID 866864281-Cyclopentyl 1-{[3-(bromomethyl)benzyl]amino}cyclopentanecarboxylateAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 63651,1-DichloroethaneLösungsmittel

Versuchsvorschrift

To a solution of 3-(bromomethyl)-benzaldehyde (0.467 g, 2.44 mmol) in dichloroethane (20 mL) was added cycloleucine cyclopentyl ester (0.802 g, 4.06 mmol) and sodium triacetoxyborohydride (1.18 g, 5.56 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 (0.568 g, 61% yield). LC/MS: m/z 380/382 [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-a5cf8c47bc324d9b8255c00db019dcb4
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321718B2

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