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

HRID 578934Notes

Reaction equation

HRID 578934 reaction equation
[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

Participants

8

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 11026Titanium isopropoxideCatalystHCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-7c463b0bb78f4bb9a1252b31e17964b6
Source dataset
uspto-grants-2015_05
Patent number
US09040522B2

Reaction notes

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