Ethyl Acetate → 5-tert-Butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate

HRID 448261노트

반응식

HRID 448261 반응식
[NH2:1][C:2]1[NH:6][N:5]=[C:4]2[C:7]([CH3:18])([CH3:17])[N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C:3]=12.C(N(CC)C(C)C)(C)C.[CH3:28][CH2:29][O:30][C:31](C)=[O:32]>C1COCC1>[NH2:1][C:2]1[N:6]([C:31]([O:30][CH2:29][CH3:28])=[O:32])[N:5]=[C:4]2[C:7]([CH3:18])([CH3:17])[N:8]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:9][C:3]=12

참가 물질

5

반응물 3

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 178451523HCID 178451523, 화합물

생성물 1

HCID 575232455-tert-Butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate수율 38%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

15 g of tert-Butyl 3-amino-6,6-dimethyl-2,6-dihydropyrrolo[3,4-c]pyrazole-5(4H)-carboxylate (59.4 mmol) were dissolved in anhydrous THF (150 ml) and treated, at 0° C. under Ar atmosphere, first with N,N-diisopropylethylamine (50 ml) and then with ClCO2 Et (4.65 ml, 1 eq.) dropwise. 90 minutes later, the solvent was diluted with EtOAc (1 l), washed with water and then with brine, dried over sodium sulfate and evaporated. The crude product was purified by flash chromatography (hexane/EtOAc 2/8) to afford 7.3 g of 5-tert-butyl 2-ethyl 3-amino-6,6-dimethylpyrrolo[3,4-c]pyrazole-2,5(4H,6H)-dicarboxylate as the major compound in 38% yield, together with 5.7 g of 5-tert-butyl 1-ethyl 3-amino-6,6-dimethyl-4,6-dihydropyrrolo[3,4-c]pyrazole-1,5-dicarboxylate in 30% yield.

후처리

  1. washwashed with water
  2. dry with materialwith brine, dried over sodium sulfate
  3. customevaporated
  4. customThe crude product was purified by flash chromatography (hexane/EtOAc 2/8)

출처 및 근거

ORD 기록
ord-86af1f73abaf4833aad398d7c434cc0a
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08481585B2

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