Hydrazine hydrate (1:1) → 1,1-Dimethylethyl 1,2,3,4,5,7-hexahydro-3-oxo-6H-pyrazolo[3,4-c]pyridine-6-carboxylate

HRID 2177601Notes

Reaction equation

O=[C:2]1[CH:7]([C:8](OCC)=[O:9])[CH2:6][CH2:5][N:4]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:3]1.O.[NH2:21][NH2:22]>C(O)C>[O:9]=[C:8]1[C:7]2[CH2:6][CH2:5][N:4]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[CH2:3][C:2]=2[NH:22][NH:21]1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 1-tert-butyl 4-ethyl 3-oxopiperidine-1,4-dicarboxylate (5.0 g, 18.43 mmol) in ethanol (10 mL) was added hydrazine monohydrate (1.04 g, 20.27 mmol) via syringe. The resulting solution was heated to 80° C. and stirred overnight. A white precipitate formed after stirring overnight. The reaction was cooled to rt and solvent was decanted from the reaction mixture, the solids were dried under vacuum to provide the desired product (3.8 g, 86%). MS (ESI) mass calcd. C11H17N3O3, 239.2. m/z found, 240.2 [M+H]+. 1H NMR (500 MHz, MeOD) δ 4.40 (s, 2H), 3.67-3.54 (m, 2H), 2.40 (t, J=5.6 Hz, 2H), 1.48 (s, 9H).

Workup

customA white precipitate formed
stirringafter stirring overnight
temperatureThe reaction was cooled to rt
customsolvent was decanted from the reaction mixture
customthe solids were dried under vacuum

Sources & evidence

ORD record: ord-2f0d22c0fd0449238f22ee6c49020e57
Source dataset: uspto-grants-2015_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09066946B2

Reaction notes

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