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

HRID 241564노트

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HRID 241564 반응식
[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

참가 물질

6

반응물 4

HCID 962WaterHCID 115031Hydrazinium chlorideHCID 516892Sodium BicarbonateHCID 2756790tert-Butyl 3-cyano-4-oxopyrrolidine-1-carboxylate

생성물 1

HCID 11333571tert-Butyl 3-amino-4,6-dihydropyrrolo[3,4-c]pyrazole-5(1H)-carboxylate

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
60 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-4fff926f718a4d83b4b8008d58bdcee6
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08653059B2

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