Ammonium Hydroxide → HCID 86753730, compound

Participants

Reaction Steps

A mixture of intermediate (5) (32 g) in tetrahydrofuran (500 ml) and hydrochloric acid (50 ml) was stirred and refluxed for 30 minutes. The reaction mixture was cooled and alkalized with NH4OH. The layers were separated. The aqueous layer was extracted with tetrahydrofuran. The separated organic layer was evaporated. The residue was purified by column chromatography over silica gel (eluent: CH2Cl2 /(CH3OH/NH3) 93/7). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from acetonitrile. The precipitate was filtered off and dried (vacuum; 80° C.), yielding 6.4 g of (±)-cis-3-methoxy-4-piperidinyl 4-amino-5-chloro-2,3-dihydro-7-benzofurancarboxylate (26%) (intermediate 6).

Provenance & Evidence