Acetic Acid → 4-(Cyclopropylamino)cyclohexanol

HRID 509280

Reaktionsgleichung

Reaktionsgleichung von HRID 509280
O[CH:2]1[CH2:7][CH2:6][C:5](=[O:8])[CH2:4][CH2:3]1.[CH:9]1([NH2:12])[CH2:11][CH2:10]1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].C(O)(=O)C.[OH-].[Na+]>ClCCCl>[CH:9]1([NH:12][CH:2]2[CH2:7][CH2:6][CH:5]([OH:8])[CH2:4][CH2:3]2)[CH2:11][CH2:10]1

Komponenten

7

Edukt 5

HCID 176Acetic AcidHCID 14798Sodium HydroxideHCID 69828CyclopropylamineHCID 5437064-HydroxycyclohexanoneHCID 5049666Sodium triacetoxyborohydride

Produkt 1

HCID 674688554-(Cyclopropylamino)cyclohexanolAusbeute 96,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Versuchsvorschrift

4-hydroxycyclohexanone (443 mg, 3.88 mmol) was dissolved in 1,2-dichloroethane (20 ml), followed by sequential addition of cyclopropylamine (0.295 ml, 4.27 mmol), NaBH(OAc)3 (1.3 g, 6.21 mmol), and acetic acid (0.2 ml, 3.88 mmol), and then the resulting mixture was stirred at room temperature under nitrogen stream for 13 hours. The resulting reaction liquid was neutralized by addition of 10% aqueous NaOH solution, and extracted with 10% MeOH/MC (15 ml×4). The organic layer was dried over anhydrous sodium sulfate, followed by filtration, concentration, and vacuum drying, to obtain 580 mg of yellow solid (96%).

Aufarbeitung

  1. customThe resulting reaction liquid
  2. extractionextracted with 10% MeOH/MC (15 ml×4)
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. filtrationfollowed by filtration, concentration, and vacuum
  5. customdrying

Quellen und Nachweise

ORD-Eintrag
ord-9665846892b6482b9427b017797db0fe
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09096571B2

Verknüpfte Notizen

Wird geladen…