Water → tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate

HRID 241564Notes

Reaction equation

[C:1]([N:8]1[CH2:12][C:11](=O)[CH:10]([C:14]#[N:15])[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=O.Cl.[NH2:17][NH2:18].C([O-])(O)=O.[Na+].[OH2:24]>C(O)C>[NH2:15][C:14]1[C:10]2[CH2:9][N:8]([C:1]([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:24])[CH2:12][C:11]=2[NH:17][N:18]=1

Participants

Conditions

Temperature: 60 °C

Procedure

N-Boc-3-cyano-4-pyrrolidinone (5 g, 23.78 mmol) and hydrazine monohydrochloride (1.629 g, 23.78 mmol) were dissolved in ethanol (140 ml). The mixture was heated to 60° C. for 3 h. The mixture was cooled to 0° C. and saturated aqueous NaHCO3 (50 mL) was added slowly, remaining water was extracted four times with ethyl acetate. The organic phase was dried over Na2SO4 (anhydrous). The residue was purified by column chromatography on silica gel Biotage 40M, eluting with EtOAc/MeOH/aqueous ammonia (gradient from 0 to 10%) to give the title product as a yellow foam. LC-MS: 224.99 (M+1).

Workup

temperatureThe mixture was cooled to 0° C.
extractionwas extracted four times with ethyl acetate
dry with materialThe organic phase was dried over Na2SO4 (anhydrous)
customThe residue was purified by column chromatography on silica gel Biotage 40M
washeluting with EtOAc/MeOH/aqueous ammonia (gradient from 0 to 10%)

Sources & evidence

ORD record: ord-4fff926f718a4d83b4b8008d58bdcee6
Source dataset: uspto-grants-2014_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08653059B2

Reaction notes

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