Reaktion #427358

Reaktionsgleichung

acetic acid

bicarbonate

bicarbonate

tert-butyl[(3S,5S,6R)-2-hydrazinylidene-6-methyl-5-phenylpiperidin-3-yl]carbamate

1-(trifluoromethyl)cyclopropanecarboxylic acid

1-hydroxy-7-azabenzotriazole

N-methylmorpholine

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

→

crude title compound

tert-Butyl{(5R,6S,8S)-5-methyl-6-phenyl-3-[1-(trifluoromethyl)cyclopropyl]-5,6,7,8-tetrahydro[1,2,4]triazolo[4,3-a]pyridine-8-yl}carbamate

Lösungsmittel

Acetonitrile

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionthe resulting mixture was extracted with ethyl acetate (3×)
2. 2
   WaschenThe combined organic extracts were washed with brine
3. 3
   Trocknendried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Einengenconcentrated
6. 6
   workup.STIRRINGthe resulting mixture stirred at 70° C. for 90 min
7. 7
   Extraktionthe resulting mixture was extracted with ethyl acetate (3×)
8. 8
   WaschenThe combined organic extracts were washed with brine
9. 9
   Trocknendried over magnesium sulfate
10. 10
    Filtrationfiltered
11. 11
    Einengenconcentrated

Vorschrift

To a solution of crude tert-butyl[(3S,5S,6R)-2-hydrazinylidene-6-methyl-5-phenylpiperidin-3-yl]carbamate (99 mg, 0.31 mmol) in dichloromethane (3.1 mL) was added 1-(trifluoromethyl)cyclopropanecarboxylic acid (58 mg, 0.37 mmol), 1-hydroxy-7-azabenzotriazole (4.3 mg, 0.031 mmol), N-methylmorpholine (82 μL, 0.75 mmol) and 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (72 mg, 0.37 mmol). The mixture was stirred 1 h. Saturated aqueous bicarbonate was added, and the resulting mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated. Acetonitrile (12.5 mL) and glacial acetic acid (18 μL, 0.31 mmol) were added and the resulting mixture stirred at 70° C. for 90 min. Saturated aqueous bicarbonate was added, and the resulting mixture was extracted with ethyl acetate (3×). The combined organic extracts were washed with brine, dried over magnesium sulfate, filtered and concentrated giving the crude title compound. MS 437.2 (M+1),

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