Tert-Butylamine → methyl 3-(tert-butylamino)-2,3-dihydro-1H-indene-5-carboxylate

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Reaction Steps

A solution of methanesulfonic acid anhydride (6.79 g, 39.062 mmol, 2.5 eq.) in DCM (20 ml) was added dropwise at −78° C. to a solution of methyl 3-hydroxy-2,3-dihydro-1H-indene-5-carboxylate (3.0 g, 15.625 mmol, 1.0 eq.) and TEA (11.0 ml, 78.125 mmol, 5.0 eq.) in DCM (60 ml) and stirred for 2 hours at the same temperature. tert-Butylamine (16 ml, 156.5 mmol, 10.0 eq.) was slowly added dropwise at −78° C., and the mixture was heated to RT and stirred for 14 hours. The reaction solution was diluted with DCM (100 ml), washed with water (2×50 ml) and sat. NaCl solution (50 ml), dried over sodium sulfate, concentrated under reduced pressure and purified by column chromatography (silica gel, 13% ethyl acetate in hexane). Yield: 32% (1.2 g, 4.858 mmol)

Provenance & Evidence