Carbon Dioxide → N-((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide

A mixture of N-((S)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide (10.0 g) and THF (130 ml) was cooled to −78° C. (dry ice bath) and a solution of methyl lithium (18.9 ml; 1.6 M in diethyl ether) was added dropwise. One minute after the addition had ended, a solution of butyllithium (13.9 ml; 2.5 M in toluene) was added dropwise. One minute after the addition had ended, DMF (5.1 g) was added, and, after a further 30 seconds, acetic acid (4.5 ml). After warming to room temperature, the reaction mixture was diluted with water and extracted with ethyl acetate. The organic phases were dried over magnesium sulfate and concentrated. The product was thus obtained with the molecular weight of 379.46 (C23H25NO4); MS (ESI): 380 (M+H+). In an analogous manner, N-((R)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide was prepared from N-((R)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-[(S)-1-(tetrahydrofuran-2-yl)methoxy]benzamide.

1. additionOne minute after the addition
2. additionOne minute after the addition
3. extractionextracted with ethyl acetate
4. dry with materialThe organic phases were dried over magnesium sulfate
5. concentrationconcentrated
6. customThe product was thus obtained with the molecular weight of 379.46 (C23H25NO4)

ORD record

ord-54d188d6fc6541219542492bf213711e

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08609731B2