Dimethylformamide → (+/-)-trans-2-Amino-1-[2-(carboxy)ethylthio]-cyclohexane

Temperatur

60 °C

(±)-7-(tert-Butoxycarbonyl)-7-aza-bicyclo-[4.1.0]- cycloheptane (0.5 g, 2.68 mmol) was dissolved in 2 mL dimethylformamide and βmercaptopropionic acid (0.318 g, 3 mmol). After the addition of cesium carbonate (1.95 g, 6 mmol), the mixture was stirred at 60° C. until the TLC indicated the full consumption of starting material (appro. 4 hrs). The reaction mixture was diluted with water, the pH was adjusted to 4 (with 2.4 M HCl) and finally extracted with methylene chloride. The solvent layer was washed with brine, dried and evaporated to give the crude (±)-trans-2-(tert-butocycarbonylamino)-1-[2-(carboxy)ethylthio]-cyclohexane, which was not purified but taken to the next stage. The crude from the above was dissolved in 10 ml ethyl acetate saturated with hydrogen chloride and stir at room temperature. The white precipitate that resulted was filtered and dried under vacuo yielding 0.636 g of (±)-trans-2-amino-1-[2-(carboxy)ethylthio]-cyclohexane.

1. customthe full consumption of starting material (appro. 4 hrs)
2. additionThe reaction mixture was diluted with water
3. extractionfinally extracted with methylene chloride
4. washThe solvent layer was washed with brine
5. customdried
6. customevaporated
7. customto give the crude (±)-trans-2-(tert-butocycarbonylamino)-1-[2-(carboxy)ethylthio]-cyclohexane, which
8. customwas not purified
9. dissolutionThe crude from the above was dissolved in 10 ml ethyl acetate saturated with hydrogen chloride
10. stirringstir at room temperature
11. customThe white precipitate that resulted
12. filtrationwas filtered
13. customdried under vacuo

ORD-Eintrag

ord-288cc3abeb6c4e8d93601c942af36e97

Quelldatensatz

uspto-grants-2002_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06372733B1