Phenylsilane → N-benzyl-1-phenylethylamine

関与物質

反応条件

反応手順

In a dry Schlenk tube under argon was placed (R,R)-Ethylene-1,2-bis(η5 -4,5,6,7-tetrahydroindenyl) titanium (R)-1,1'-binaphth-2,2'-diolate (25 mg, 0.042 mmol) and THF (4 mL). A solution of n-butyllithium (53 μL, 0.084 mmol, 1.6M in hexane) was added and the mixture was stirred for 10 minutes, at which time the color was a dark shade of brown. Phenylsilane (13 μL, 0.105 mmol) was then added and the mixture was stirred for another 10 minutes, the color changing to a darker shade of brown. Acetophenone N-benzyl imine (87 mg, 0.42 mmol) was then added and the reaction vessel was sealed and moved to a dry box. The reaction mixture was transferred to a Parr high pressure reactor, which was sealed and removed from the dry box. The reactor was charged with hydrogen to 1900 psi and heated to 65° C. After stirring for 48 hours the mixture was opened to air and concentrated. The residue was diluted with diethyl ether (20 mL) and extracted with 1N HCl (3×10 mL). The combined aqueous layers were basified with NaOH until strongly basic to pH paper and extracted with diethyl ether (4×25 mL). The organic layers were combined, dried over sodium sulfate and concentrated to produce 82-89% yield of N-benzyl-1-phenylethylamine. The enantiomeric excess (ee), as determined by HPLC analysis of the free amine using a Chiralcel OD column, was 89-92% in favor of the (R)enantiomer.

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