Boron trifluoride → α-Cyclopropyl-6-methoxy-N-(phenylmethoxy)-2-pyridinemethanamine

HRID 1768435Notes

Reaction equation

HRID 1768435 reaction equation
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[N:8]=1.[CH2:15]([O:22][N:23]=[CH:24][CH:25]1[CH2:27][CH2:26]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.B(F)(F)F.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C1(C)C=CC=CC=1.O>[CH2:15]([O:22][NH:23][CH:24]([CH:25]1[CH2:27][CH2:26]1)[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][CH3:14])[N:8]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

9

Reactant 5

HCID 6356Boron trifluorideHCID 10340Sodium CarbonateHCID 2568102-Bromo-6-methoxypyridineHCID 73885307HCID 73885307, compoundHCID 178418339Butyllithium

Product 1

HCID 22398671α-Cyclopropyl-6-methoxy-N-(phenylmethoxy)-2-pyridinemethanamine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

8.8 ml (22 mmol) of n-BuLi (2.5 M in toluene) were added to 3.76 g (20 mmol) of 2-bromo-6-methoxypyridine in 20 ml of THF at −78° C. After 30 min, this dark red solution was added to a solution of 1.4 g (8 mmol) of cyclopropanecarbaldehyde O-benzyloxime (see a) and 2.52 ml (20 mmol) of BF3 etherate in 40 ml of toluene which had been stirred at −78° C. for 15 min. The mixture was stirred at −78° C. for 4 h, slowly warmed to RT and, after addition of water, made alkaline with saturated Na2CO3 solution.

Workup

  1. stirringThe mixture was stirred at −78° C. for 4 h
  2. temperatureslowly warmed to RT

Sources & evidence

ORD record
ord-927ef5cbf87043c88e0446e68d28992e
Source dataset
uspto-grants-2007_06
Patent number
US07235690B2

Reaction notes

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