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

HRID 578934ノート

反応式

HRID 578934 の反応式
[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

参加物

8

反応物 3

HCID 8000Boron trifluoride etherateHCID 11815837Oxane-4-carbonitrileHCID 178418443HCID 178418443、化合物

生成物 1

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

試薬・触媒・溶媒 4

HCID 11026Titanium isopropoxide触媒HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒HCID 3283Diethyl Ether溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-7c463b0bb78f4bb9a1252b31e17964b6
出典データセット
uspto-grants-2015_05
特許番号
US09040522B2

反応ノート

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