HCID 86729462, compound → (1R,5S)-3-benzyl-N,N-dimethyl-3-azabicyclo[3.1.0]hexan-1-amine

Participants

Reaction Steps

To a solution of 2-(allyl(benzyl)amino)-N,N-dimethylacetamide (0.57 g, 2.45 mmol, 1.0 eq) in anhydrous THF (25 mL) at room temperature under N2 was added ClTi(OiPr)3 (2.45 mL, 2.45 mmol, 1.0 eq) followed by i-PrMgBr (1.0M in ether, 11.0 mL, 11.0 mmol, 4.5 eq) via a syringe pump over 1 h. The reaction mixture was stirred for another 2 h, and then quenched with a small amount of water. The mixture was extracted with EtOAc (20 mL×3), the combined organic phases were washed with water and brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (30:1 (v/v) CH2Cl2/CH3OH) to give the title compound as colorless oil (0.33 g, 63%). The compound was characterized by the following spectroscopic data: MS (ESI, pos. ion) m/z: 217.35 (M+1).

Provenance & Evidence