Diisopropylethylamine → (1R)-1'-({1-[4-(Pyridin-4-ylmethoxy)phenyl]cyclopropyl}-carbonyl)-3H-spiro[2-benzofuran-1,3'-pyrrolidin]-3-one

A mixture of 1-(4-hydroxyphenyl)cyclopropanecarboxylic acid (0.20 g, 1.1 mmol), [(1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonic acid-(1R)-3H-spiro[2-benzofuran-1,3′-pyrrolidin]-3-one salt (0.47 g, 1.1 mmol), Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate (0.55 g, 1.2 mmol), and N,N-diisopropylethylamine (0.49 ml, 2.8 mmol) in methylene chloride (3 ml) was stirred at r.t. overnight. Then the reaction was quenched with water, and the reaction mixture was extracted with ethyl acetate. The extract was washed with 1N HCl aqueous solution (×2), water and brine successively; then dried over Na2SO4; and then filtered. The filtrate was concentrated to afford the desired product (0.35 g, yield: 89%).

1. customThen the reaction was quenched with water
2. extractionthe reaction mixture was extracted with ethyl acetate
3. washThe extract was washed with 1N HCl aqueous solution (×2), water and brine successively
4. dry with materialthen dried over Na2SO4
5. filtrationand then filtered
6. concentrationThe filtrate was concentrated

ORD record

ord-28bceb37479c43b4acdf20f02d346a4e

Source dataset

uspto-grants-2007_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07304081B2