Carbon Dioxide → 4-Cyclopropylmethoxy-N-((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide

A mixture of N—((S)-6-bromo-1,2,3,4-tetrahydronaphthalen-2-yl)-4-cyclopropylmethoxy-benzamide (5.20 g) and THF (120 ml) was cooled to −78° C. (dry ice bath), and a solution of methyllithium (8.9 ml; 1.6 M in diethyl ether) was added dropwise. One minute after the addition had ended, a solution of butyllithium (5.7 ml; 2.5 M in toluene) was added dropwise. One minute after the addition had ended, DMF (2.85 g) and, after a further 30 seconds, acetic acid (1.5 ml) were added. 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 349.43 (C22H23NO3); MS (ESI): 350 (M+H+). 4-Butoxy-N—((S)-6-formyl-1,2,3,4-tetrahydronaphthalen-2-yl)benzamide can also be prepared analogously.

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 349.43 (C22H23NO3)

ORDレコード

ord-cc7811fedaf243c5956de8e4b083cd4b

出典データセット

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08841290B2