Sodium cyanoborohydride → 1-tert-butyl 4-methyl 3-((1-(tert-butoxycarbonyl)-4-ethylpiperidin-4-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate

HRID 1627084노트

반응식

HRID 1627084 반응식
[CH:1]([C:3]1[C:11]2[C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=[N:7][C:6]=2[N:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:4]=1)=O.[NH2:23][C:24]1([CH2:37][CH3:38])[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26][CH2:25]1.C([BH3-])#N.[Na+]>CO.C(O)(=O)C>[C:33]([O:32][C:30]([N:27]1[CH2:26][CH2:25][C:24]([NH:23][CH2:1][C:3]2[C:11]3[C:10]([C:12]([O:14][CH3:15])=[O:13])=[CH:9][CH:8]=[N:7][C:6]=3[N:5]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:4]=2)([CH2:37][CH3:38])[CH2:29][CH2:28]1)=[O:31])([CH3:34])([CH3:36])[CH3:35]

참가 물질

6

반응물 3

HCID 5003444Sodium cyanoborohydrideHCID 45095672Tert-butyl 4-amino-4-ethylpiperidine-1-carboxylateHCID 582935211-tert-Butyl 4-methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate

생성물 1

HCID 672244961-tert-butyl 4-methyl 3-((1-(tert-butoxycarbonyl)-4-ethylpiperidin-4-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate수율 35.5%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 887Methanol용매

실험 절차

1-tert-Butyl 4-methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate (211 mg, 0.692 mmol) was dissolved in MeOH (10 mL) and tert-butyl 4-amino-4-ethylpiperidine-1-carboxylate (158 mg, 0.692 mmol) were added followed by 2 drops of acetic acid. The solution was allowed to stir at room temperature for 2 h. Then sodium cyanoborohydride (44 mg, 0.692 mmol) was added over the course of 6 h at room temperature. The solution was quenched with water and extracted with ethyl acetate. The organics were dried over MgSO4 and concentrated in vacuo. Purification by silica gel chromatography (70% EtOAc/Hexanes) gave 127 mg of 1-tert-butyl 4-methyl 3-((1-(tert-butoxycarbonyl)-4-ethylpiperidin-4-ylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate. [M+H] found 417.

후처리

  1. customThe solution was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organics were dried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customPurification by silica gel chromatography (70% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-7e776099fe74473c8bafd441877d3fb5
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785429B2

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