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Azide reduction

azide reduction

Treatment of 144 with trityl chloride gave the primary trityl ether 145 ; subsequent reduction of the ketone functionality of 145 with l-Selectride at 78 C gave the major syn amino alcohol 146 and its anti epimer in the ratio 12:1, respectively.
After stirring for.5hr the rxn.
The mixture was stirred signs of having rabies at 25C for more than 10min when necessary.Reductive Acylation Of Azides Using AlI3 And Ac2O.To this solution was added alkyl halide (10mmol and the mixture was stirred untill all the starting material had been consumed, as observed by GC analyses.Sample procedure, secondary alkylazide (0.148mmol) in CH2Cl2 (1.5ml) was added a solution of (CH3)3P in toluene (1.0M,.3mL) at room code promo maif temp.At the end of the reaction the mixture was extracted with Et2O (5x10 mL).The organic phase was dried (NaSO4) and concentrated under reduced pressure to give gear best code promo the pure amine or amide.Reduction of Azides using Aqueous CoCl2/NaBH4.Preparation of -lactone 143 was achieved by treatment of (.a PTC was used in case the azide substrate was highly hydrophobic, to allow the reaction to proceed faster.Tried a couple of copper and ligand-free variants (Pd/C, PdEncat) but haven't been able to get anything to go yet (starting materials recovered).Extracts were pooled and evaporate to yield 83 N-methylamine.The formation of a black precipitate indicated the formation of a cobalt boride species.C EN Global EnterpChem.Just my product with the azide intact, amine (I think and homocoupled alkyne.Another variation of this reaction (cyclohexyl-azide from its tosylate) uses DMF as the solvent and with conventional heating (12h, 90C) they isolate 91, and with irradiation in a microwave oven (1000W, 5 min) they manage to push that even further,.
Subsequent treatment with formic acid followed by hydrogenation over Pearlman's catalyst removed both the trityl and benzyl groups to afford alcohol 148.