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

HRID 241564ノート

反応式

HRID 241564 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
60 °C

実験手順

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).

後処理

  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%)

出典と根拠

ORDレコード
ord-4fff926f718a4d83b4b8008d58bdcee6
出典データセット
uspto-grants-2014_02
特許番号
US08653059B2

反応ノート

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