8-Methyl-8-azabicyclo(3.2.1)octan-3-ol → 8-Azabicyclo(3.2.1)octan-3-ol, 8-methyl-, 3-methanesulfonate

Temperatur

20 °C

Tropine (50 g) and triethylamine (60 mL, 43.56 g) in dichloromethane (1 L) were cooled to −10° C. Methane sulphonyl chloride (36 mL, 53.28 g) in dichloromethane (0.2 L) was added over 1 h at −5+/−2° C. After 0.5 h a solution of potassium carbonate (150 g) in water (0.4 L) was added and the mixture warmed to 20° C. The phases were separated and the aqueous phase extracted with further dichloromethane (1×0.2 L). The combined dichloromethane solution was concentrated by distillation collecting 1 L. n-Heptane (0.875 L) was added and the mixture stirred for 0.5 h. The solution was decanted off and then concentrated by distillation at 610 to 650 mbar until a solution temperature of 63° C. was reached. The solution was cooled to 0° C. with crystallization occurring during the cooling. The mixture was stirred for 1 h, the product isolated by filtration, washed and dried at <30° C. to give the title compound (60.62 g, 78.1%).

1. customThe phases were separated
2. extractionthe aqueous phase extracted with further dichloromethane (1×0.2 L)
3. concentrationThe combined dichloromethane solution was concentrated by distillation
4. customcollecting 1 L
5. additionn-Heptane (0.875 L) was added
6. customThe solution was decanted off
7. concentrationconcentrated by distillation at 610 to 650 mbar until a solution temperature of 63° C.
8. temperatureThe solution was cooled to 0° C. with crystallization
9. stirringThe mixture was stirred for 1 h
10. customthe product isolated by filtration
11. washwashed
12. customdried at <30° C.

ORD-Eintrag

ord-3f02659a912c4bbdaf5ea287d5bb31b1

Quelldatensatz

uspto-grants-2012_06

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08207191B2