Tetrahydrofuran → (2R,3R,4R,6R)-2-Diphenylmethyl-3-(2-methoxybenzylamino)-6-phenethyl-1-azabicyclo[2.2.2]octane

Participants

Role	Name	HCID	Charge
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	9-Borabicyclo(3.3.1)nonane	HCID 78966	—
Reactant	2-Methoxybenzylamine	HCID 81292	—
Reactant	(2R,4R,6R*)-2-Diphenylmethyl-6-phenethylquinuclidin-3-one	HCID 54156123	—
Catalyst	Bicyclo[2.2.1]heptane-1-methanesulfonic acid, 7,7-dimethyl-2-oxo-, (1S)-	HCID 18462	—
Solvent	Toluene	HCID 1140	—
Product	(2R,3R,4R,6R)-2-Diphenylmethyl-3-(2-methoxybenzylamino)-6-phenethyl-1-azabicyclo[2.2.2]octane	HCID 70115251	23.3%

Reaction Steps

Compound 7 (357 mg, 0.904 mmol), 2-methoxybenzylamine (189 mg, 1.38 mmol) and camphorsulfonic acid (2.0 mg) were dissolved in toluene (30 ml), and the resultant mixture was heated at reflux for 3 days under a dehydrating condition with MS 4A. After replacement of the solvent with THF a solution of 9-BBN (0.5M in THF, 5.4 ml) was added, and the resultant mixture was stirred for 4 days at room temperature. After evaporation of the solvent the residue was basified at pH=13, extracted with CH2Cl2, dried over Na2SO4, and concentrated down. The crude material was purified by combination of column chromatography (silica-gel, MeOH/CH2Cl2), preparative TLC (silica-gel, 10% MeOH/CH2 Cl2) and crystallization from MeOH to provide pure compound 8 (109 mg, 23%).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05716965
Source dataset	uspto-grants-1998_02
ORD ID	ord-1a9900c299204e34bea8d0b7814da216
Source note	uspto-grants-1998_02