1,1'-Carbonyldiimidazole → (3aR,4S,7aR)-7,7-diphenyl-2-[(S)-2-(2-methoxyphenyl)propionyl]-4-perhydroisoindolol

温度

4 °C

0.37 g of carbonyldiimidazole is added to a solution, cooled to +4° C., of 0.41 g of (S)-2-(2-methoxyphenyl)-propionic acid in 15 cm3 of dry dichloromethane. The mixture is stirred for one hour at 4° C. and then a solution of 0.75 g (3aR,4S,7aR)-7,7-diphenyl-4-perhydroiso-indolol hydrochloride is added. The reaction mixture is stirred at room temperature for 20 hours and then then washed twice with 10 cm3 of water, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 3.6 cm, height 37 cm), eluting under a nitrogen pressure of 0.5 bar with an ethyl acetate and cyclohexane mixture (50/50 by volume) and collecting fractions of 50 cm3. Fractions 21 to 41 are pooled and concentrated to dryness under reduced pressure (2.7 kPa). The residue is triturated in isopropyl oxide and then dried. 0.3 g of (3aR,4S,7aR)-7,7-diphenyl-2-[(S)-2-(2-methoxyphenyl)propionyl]-4-perhydroisoindolol is obtained in the form of a white meringue.

1. stirringThe reaction mixture is stirred at room temperature for 20 hours
2. washwashed twice with 10 cm3 of water
3. dry with materialdried over magnesium sulphate
4. filtrationfiltered
5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
6. customThe residue is chromatographed on a silica gel column (particle size 0.04-0.06 mm, diameter 3.6 cm, height 37 cm)
7. washeluting under a nitrogen pressure of 0.5 bar with an ethyl acetate and cyclohexane mixture (50/50 by volume)
8. customcollecting fractions of 50 cm3
9. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
10. customThe residue is triturated in isopropyl oxide
11. customdried

ORDレコード

ord-83dfa1ec68c84488a5a89b4b9fe82dc3

出典データセット

uspto-grants-1995_09

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US05451601