tert-butyl 4-formyl-1,3-dihydroisoindole-2-carboxylate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 350 mg of tert-butyl 4-formyl-1,3-dihydro-2H-isoindole-2-carboxylate in 11 mL of methanol was added 134 mg of sodium borohydride under ice-cooling, followed by stirring at room temperature overnight. To the reaction mixture were added water and ethyl acetate and the aqueous layer was separated. The obtained organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to obtain 213 mg of tert-butyl 4-(hydroxymethyl)-1,3-dihydro-2H-isoindole-2-carboxylate as a yellow oil. cooling the aqueous layer was separated The obtained organic layer was washed with saturated brine dried over anhydrous magnesium sulfate The solvent was evaporated under reduced pressure

Conditions: temp:60.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of 238 mg of tert-butyl 4-formyl-1,3-dihydro-2H-isoindole-2-carboxylate, 612 mg of sodium triacetoxyborohydride, 963 μL of a 2 M dimethylamine-tetrahydrofuran solution, 12 μL of acetic acid, and 14 mL of 1,2-dichloroethane was stirred at 60° C. overnight. After cooling to room temperature, to the reaction mixture was added a saturated aqueous sodium hydrogen carbonate solution, and chloroform was added and the aqueous layer was separated. The obtained organic layer was washed with saturated brine and then dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate) to obtain 123 mg of tert-butyl 4-[(dimethylamino)methyl]-1,3-dihydro-2H-isoindole-2-carboxylate as an orange oil. After cooling to room temperature, to the reaction mixture was added the aqueous layer was separated The obtained organic layer was washed with saturated brine dried over anhydrous magnesium sulfate the solvent was evaporated under reduced pressure The obtained residue was purified by silica gel column chromatography (n-hexane/ethyl acetate)