Triethylborane → Cyclopropyl m-ethylbenzylamine
Reaction equation
[C:1]([N:8](Br)[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)(OC(C)(C)C)=O.[O-]P([O-])([O-])=O.[K+].[K+].[K+].[CH2:25](B(CC)CC)[CH3:26].[CH2:32]1COC[CH2:33]1>>[CH:1]1([NH:8][CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([CH2:32][CH3:33])[CH:15]=2)[CH2:26][CH2:25]1Participants
5
Procedure
The Boc-bromobenzyl amine 10 (26.8 g, 94.03 mmol), and PddfPdC12 (816 mg, 0.38 mmol, 0.004 eq) were mixed together in anhydrous THF (300 mL) and aqueous K3PO4 (100 mL of 2.0 M). To this red solution was added triethylborane (100 ml of 1.0 M in THF, 100 mmol). The solution turned black and was refluxed for 4 hours. GC/MS indicated the reaction was complete. The solution was poured into a separatory funnel and the aqueous layer separated. The organic layer was collected and solvent removed to a volume of 100 mL. Ethyl acetate/ hexanes (300 mL of 1:1) were added and the solution was extracted with 1N HCl (1×100 mL), sodium bicarbonate (2×100 mL) and brine (1×100 mL). The solution was dried over sodium sulfate and vacuum filtered through a bed of silica gel (125 ml of silica). The solvent was removed at reduced pressure to afford 20.6 grams of 11 as light yellow oil.