1,2-Dichloroethane → 8-(1-Benzyl-4-(SR)-phenylpyrrolidin-3-(RS)-ylmethyl)-2-(4-bromobenzyl)-2,8-diaza-spiro[4.5]decan-1-one dihydrochloride

Participants

Reaction Steps

A solution of 28.9 mg (60 μmol) of 2-(4-bromobenzyl)-8-(4-(SR)-phenylpyrrolidin-3-(RS)-ylmethyl)-2,8-diaza-spiro[4.5]decan-1-one and 6.3 mg (60 μmol) of benzaldehyde in 1.5 mL of DCE was agitated for 10 minutes at room temperature before adding 20 mg (90 μmol) of triacetoxyborohydride. The reaction mixture was then stirred overnight and quenched with a saturated solution of sodium bicarbonate (1 mL). The solution was extracted with DCM (2×2 mL) and the combined organic layers were concentrated. The crude was purified by semi-preparative HPLC (method B) yielding 15.3 mg (39.5%) of Compound 98 as a pale yellow solid.

Provenance & Evidence