Ammonia → 1-Azabicyclo[3.3.1]nonane-5-carboxamide

Temperatur

150 °C

A solution of 1-azabicyclo[3.3.1]nonane-5-carboxylic acid methyl ester (1.83 g, 10 mmol) in ammonia (50 mL) and methanol (20 mL) was sealed in a bomb and heated at 120°-130° C. for 36 hours (gas chromatography indicated that the reaction was incomplete). Three drops of 25% sodium methoxide/methanol were added, and the mixture was heated at 130° C. for 21 hours and at 150° C. for 72 hours, at which time the reaction was essentially complete. The solution was concentrated in vacuo and the residue was partitioned between 1.25N sodium carbonate (50 mL) and methylene chloride (75 mL). The organic layer was separated and the aqueous solution was extracted with methylene chloride (2×40 mL). The combined organic layers were dried (Na2SO4), concentrated in vacuo, and recrystallized from acetonitrile to afford 0.64 g (38%) of pale brown solid; mp 172.5°-175.0° C.

1. temperatureheated at 120°-130° C. for 36 hours (gas chromatography
2. concentrationThe solution was concentrated in vacuo
3. customthe residue was partitioned between 1.25N sodium carbonate (50 mL) and methylene chloride (75 mL)
4. customThe organic layer was separated
5. extractionthe aqueous solution was extracted with methylene chloride (2×40 mL)
6. dry with materialThe combined organic layers were dried (Na2SO4)
7. concentrationconcentrated in vacuo
8. customrecrystallized from acetonitrile

ORD-Eintrag

ord-37ba75b1b1944de596d5785b37bb6bfe

Quelldatensatz

uspto-grants-1993_09

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05244907