HCID 86729462, compound → (1R,5S)-3-benzyl-N,N-dimethyl-3-azabicyclo[3.1.0]hexan-1-amine
Reaction equation
[CH2:1]([N:4]([CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:5][C:6]([N:8]([CH3:10])[CH3:9])=O)[CH:2]=[CH2:3].C([Mg]Br)(C)C>C1COCC1>[CH2:11]([N:4]1[CH2:1][C@H:2]2[C@:6]([N:8]([CH3:10])[CH3:9])([CH2:3]2)[CH2:5]1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
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).