Hydrochloric Acid → methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-4-(3-hydroxypropyl)-7H-pyrrolo(2,3-d)carbazole-6-carboxylate

Temperature

110 °C

A mixture of methyl 3-benzyl-1,2,3,4,5,6-hexahydroazepino (4,5-b) indole-5-carboxylate (1.336 g, 4.0 mmol), 2-hydroxytetrahydropyran (0.980 g, 8.2 mmol), toluene (30 mL) and ether saturated with HCl gas (10 drops) was heated under a nitrogen atmosphere at 110° C. for 5 h. The reaction mixture was cooled, diluted with 15 mL of methanol and acidified with conc. hydrochloric acid. The reaction mixture was stirred for 12 h at 20° C., poured into 50 mL of water and made strongly basic with ammonium hydroxide. The toluene layer was separated and the aqueous portion extracted three times with 25 mL of dichloromethane. The combined organic solutions were washed three times with 25 mL of saturated brine, dried over sodium sulfate and concentrated at 50° C. under vacuum to provide 1.67 g (100%) of methyl 3-benzyl-1,2,3,3a,4,5-hexahydro-4-(3-hydroxypropyl)-7H-pyrrolo(2,3-d)carbazole-6-carboxylate, identical in spectroscopic properties and TLC Rf value to the product obtained in Example 1.

1. temperatureThe reaction mixture was cooled
2. customThe toluene layer was separated
3. extractionthe aqueous portion extracted three times with 25 mL of dichloromethane
4. washThe combined organic solutions were washed three times with 25 mL of saturated brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated at 50° C. under vacuum

ORD record

ord-d2165c8dbe0f4da0b7248038b46147f5

Source dataset

uspto-grants-1989_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04841045