Hydrochloric Acid → 1H-Cyclopropa[4,5]cyclopenta[1,2]pyrazole-3-carboxylic acid, 4,4a,5,5a-tetrahydro-, ethyl ester, (4aR,5aR)-
Reaction equation
[C@@H:1]12[CH2:6][C@@H:5]1[CH2:4][CH2:3][C:2]2=O.CC(C)([O-])C.[K+].[C:14](OCC)(=O)[C:15]([O:17][CH2:18][CH3:19])=[O:16].[NH2:24][NH2:25].Cl>C(O)C>[CH2:6]1[C@@H:5]2[CH2:4][C:3]3[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:24][NH:25][C:2]=3[C@H:1]12Participants
7
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 70 °C
Procedure
(1R,5S)-Bicyclo[3.1.0]hexan-2-one (1.000 g, 10.40 mmol) was taken up in ethanol (40 mL) and potassium tert-butoxide (1.0 M in THF) (13.00 mL, 13.00 mmol) was added, followed by diethyl oxalate (1.413 mL, 10.40 mmol). The resulting solution was heated and stirred for 1 h at 70° C. Hydrazine (10.40 mL, 10.40 mmol) was then added, followed by hydrochloric acid (ca 3 M aqueous) (10.40 mL, 31.2 mmol). The solution was stirred at 70° C. for 1 h and purified by HPLC to give the title compound (356 mg, 1.852 mmol, 17.80% yield) as a solid. LCMS m/z=193.3 [M+H]+.
Workup
- temperatureThe resulting solution was heated
- stirringThe solution was stirred at 70° C. for 1 h
- custompurified by HPLC
Sources & evidence
- ORD record
- ord-b0669d0a1ba94091b5b604e055ddcd02
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08778950B2
Reaction notes
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