Reaktion #1974263

Reaktionsgleichung

NaOH

L-proline

NaN3

4-(5-Bromo-isoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl ester

→

compound 31

Ausbeute 123.4%

6-(Piperidin-4-yloxy)-isoquinolin-5-ylamine

Ausbeute 123.4%

Lösungsmittel

ethanol water

ethyl acetate

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwere added
2. 2
   Filtrationthe mixture was filtered through a celite cartridge
3. 3
   SonstigeAfter removal of the solvents
4. 4
   workup.DISTILLATIONby distillation the remainder
5. 5
   workup.ADDITIONThen water was added
6. 6
   Sonstigeall solvents were removed by freeze
7. 7
   Sonstigedrying

Vorschrift

60 μL of 1 N NaOH-solution, 6.9 mg (0.3 eq) of L-proline, 3.8 mg (0.1 eq) of CuI and 26 mg (0.4 mmol) of NaN3 were added to a solution of 82 mg (0.2 mmol) of 4-(5-Bromo-isoquinolin-6-yloxy)-piperidine-1-carboxylic acid tert-butyl ester (11) in 2 mL of ethanol/water (7/3). The mixture was heated to 95° C. for 3 h in a microwave reactor (CEM Discover). After cooling water and ethyl acetate were added and the mixture was filtered through a celite cartridge. After removal of the solvents by distillation the remainder was subjected to preparative HPLC. The N-Boc-protected intermediate was deprotected by treatment with 2 mL 5-6 N HCl in isopropanol for 2 h at room temperature. Then water was added and all solvents were removed by freeze drying to yield 18 mg of compound 31 as hydrochloride.

Quelle