Boron trifluoride etherate → 1-(Tetrahydro-2H-pyran-4-YL)cyclopropanamine

HRID 526435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 526435
[O:1]1[CH2:6][CH2:5][CH:4]([C:7]#[N:8])[CH2:3][CH2:2]1.[CH2:9]([Mg]Br)[CH3:10].B(F)(F)F.CCOCC>CCOCC.O.Cl.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[O:1]1[CH2:6][CH2:5][CH:4]([C:7]2([NH2:8])[CH2:10][CH2:9]2)[CH2:3][CH2:2]1

Komponenten

8

Edukt 3

HCID 8000Boron trifluoride etherateHCID 11815837Oxane-4-carbonitrileHCID 178418443HCID 178418443, Verbindung

Produkt 1

HCID 577902951-(Tetrahydro-2H-pyran-4-YL)cyclopropanamineAusbeute 66,9 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 11026Titanium isopropoxideKatalysatorHCID 313Hydrochloric AcidLösungsmittelHCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

Combined tetrahydro-2H-pyran-4-carbonitrile (1.000 g, 9.00 mmol) and titanium (IV)isopropoxide (2.90 mL, 9.90 mmol) in ether (45.0 mL), then ethylmagnesium bromide (6.60 mL, 19.79 mmol) was added and the reaction was allowed to warm to room temperature for 1 hour. The reaction was stirred for an additional 30 minutes and boron trifluoride etherate (2.280 mL, 18.0 mmol) was added and the reaction was stirred for 2 hours. The reaction was then diluted with 10 mL water and 20 mL 1 N HCl and extracted twice with 200 mL EtOAc. The organic layers were combined and concentrated to afford the title compound (850 mg, 53.5%) as a yellow oil.

Aufarbeitung

  1. stirringthe reaction was stirred for 2 hours
  2. extractionextracted twice with 200 mL EtOAc
  3. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-324d2f9cefc24e0f85048728a9e810eb
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09345713B2

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