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Deprotection of the Boc group with hydrochloric acid

WO2010049841 Reagents: Amine-Boc : 1 equivalent 4 N Hydrochloric acid/dioxane : excess Dichloromethane : solvent Deprotected amine : >90% yield expected Procedure: To a solution of the Boc protected amine (1 eq) in anhydrous dichloromethane (10 mL/ mmol of Boc-amine) was added 4N HCl in dioxane (20 eq).  The reaction was stirred at room temperature... [Read More...]

Preparation of methyl esters from carboxylic acids and diazomethane

Reagents: Carboxylic acid : 1 equivalent Diazomethane : 2eq or excess Ethyl ether : solvent Methyl ester : > 90% expected yield Procedure: The carboxylic acid is dissolved in ethyl ether (2 mL/mmol) and cooled to 0 oC.  Diazomethane ( 2 eq or excess) is added slowly and the reaction is stirred for 1h.  The excess diazomethane is destroyed by the... [Read More...]

Preparation of Phenylphthalamide from bromobenzene and phthalamide

J. Med. Chem., 1994, 37, 3434 Reagents: Nitrobromobenzene : 1 equivalent Cuprous iodide : 2 eq or excess Potassium phthalamide : 1 eq Anhydrous dimethylacetamide (DMA) : solvent Phenylphthalamide : good yields expected Procedure: To a solution of phthalamide (1 eq) in anhydrous DMA (2 mL/mmol of phthalamide) in an ice-bath is added sodium hydride (1,2... [Read More...]

Reduction of oximes to amines with titanium trichloride

To a solution of the oxime, NH4OAc, and NaCNBH3 in methanol was added TiCl3 (80%, HCl/H2O) dropwise.  The purple solution turns clear as it becomes oxidized.  TiCl3 was added until the purple coloration persisted for 10 min.  Let stir overnight.  10% NH4OH was added and stirred for 1h.  The solution (milky white) was extracted with CHCl3 (3x). ... [Read More...]

Preparation of aldehydes from benzylic alcohol oxidation using manganese dioxide

NOTE: manganese dioxide is selective for the oxidation of benzyl and allyl alcohols to the corresponding aldehyde To a solution of the alcohol in CHCl3 (10 mL/mmol) is added activated manganese dioxide (2 g/mmol), and the resultant mixture is stirred at room temperature for 2h.  The reaction mixture is filtered and washed with chloroform. The combined... [Read More...]