Hydrochloric Acid → Hydrochloric Acid

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Reaction Steps

Sodium hydride (0.048 g, 1.2 mmol, 60% dispersion in mineral oil) was added to a mixture of the above intermediate in N,N-dimethylformate (2.3 mL) under N2. The mixture was stirred at r.t. for 10 min., and methyl iodide (0.075 mL, 1.2 mmol) was added. The reaction mixture was stirred at r.t. overnight. The mixture was diluted with water, and extracted with ethyl acetate (3×10 mL). The combined organic layers were dried over MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash chromatography on a silica gel column with ethyl acetate in hexanes (0-30%) to afford tert-butyl (1S,2R)-2-methoxy-2,3-dihydro-1H-inden-1-ylcarbamate [LCMS (M+Na)+: 286.1]. 2 mL of 4 N HCl in 1,4-dioxane was added to a solution of tert-butyl (1S,2R)-2-methoxy-2,3-dihydro-1H-inden-1-ylcarbamate in methanol (1 mL). The reaction mixture was stirred at r.t. overnight. The volatiles were removed under reduced pressure to afford the desired product as HCl salt.

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