Sodium triacetoxyborohydride → (R)-6-(2-(9-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl)ethyl)-3-methylisochroman-1-one

Beteiligte Stoffe

Reaktionsschritte

A solution of 5-[(1R)-1-hydroxy-2-(3-oxa-7,9-diazabicyclo[3.3.1]non-9-yl)ethyl]-4-methyl-2-benzofuran-1(3H)-one (INTERMEDIATE 17) (60 mg, 0.19 mmol) and (R)-2-(3-Methyl-1-oxoisochroman-6-yl)acetaldehyde (INTERMEDIATE 21) (39 mg, 0.19 mmol) in 1,2-dichloroethane (5 mL) was treated with sodium triacetoxyborohydride (120 mg, 0.57 mmol) and stirred at room temperature for 1 hour. The reaction mixture was concentrated and the residue was purified by preparative TLC eluting with 5% (10% NH4OH in MeOH)/95% DCM, followed by a second preparative TLC iteration eluting with 5% (10% NH4OH in MeOH)/95% chloroform (eluted twice) to provide (R)-6-(2-(9-((R)-2-hydroxy-2-(4-methyl-1-oxo-1,3-dihydroisobenzofuran-5-yl)ethyl)-3-oxa-7,9-diazabicyclo[3.3.1]nonan-7-yl)ethyl)-3-methylisochroman-1-one.

Herkunft & Nachweise