Acetonitrile → HCID 178526510, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of tert-butyl-(2-isothiocyanato-6-nitro-benzyloxy)-dimethyl -silane (intermediate 2) (3.0 g, 9.0 mmol) in acetonitrile (45 mL) at 23° C. was added R-(−)-1-aminoindane (1.24 g, 9.0 mmol) and the mixture was stirred at 23° C. for 45 min. Added tetrabutylammonium fluoride (1M in tetrahydrofurane, 9.25 mL, 9.0 mmol) and stirred at 23° C. for 1 h. Added 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC.HCl) (2.71 g, 14 mmol) and refluxed for 4.5 h. Cooled to room temperature, diluted with ethyl acetate and water, added little 1 M NaH2PO4.2H2O solution to achieve pH 4, separated phases, washed organic layer with brine and dried over sodium sulfate. Removal of the solvent in vacuum left a yellow foam, which was recrystallized from dichloromethane and diisopropylether to give the title compound as a yellow solid (1.94 g, 68%), MS (ISP) m/e=310.4 [(M+H)+].

Provenance & Evidence