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

HRID 526435노트

반응식

HRID 526435 반응식
[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

참가 물질

8

반응물 3

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

생성물 1

HCID 577902951-(Tetrahydro-2H-pyran-4-YL)cyclopropanamine수율 66.9%

시약·촉매·용매 4

HCID 11026Titanium isopropoxide촉매HCID 313Hydrochloric Acid용매HCID 962Water용매HCID 3283Diethyl Ether용매

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-324d2f9cefc24e0f85048728a9e810eb
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09345713B2

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