Reaktion #591476

Reaktionsgleichung

1-(4-hydroxyphenyl)cyclopropanecarboxylic acid

[(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

Benzotriazol-1-yloxytris(dimethylamino)phosphonium hexafluorophosphate

N,N-diisopropylethylamine

→

desired product

Ausbeute 89.0%

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

Ausbeute 89.0%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThen the reaction was quenched with water
2. 2
   Extraktionthe reaction mixture was extracted with ethyl acetate
3. 3
   WaschenThe extract was washed with 1N HCl aqueous solution (×2), water and brine successively
4. 4
   Trocknenthen dried over Na2SO4
5. 5
   Filtrationand then filtered
6. 6
   EinengenThe filtrate was concentrated

Vorschrift

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%).

Quelle