Acetic Acid → tert-butyl 4-(1H-indol-5-ylamino)piperidine-1-carboxylate

HRID 20982

반응식

HRID 20982 반응식
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[CH:5]2.[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][C:21](=O)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.O>[C:11]([O:15][C:16]([N:18]1[CH2:23][CH2:22][CH:21]([NH:1][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[CH:5]3)[CH2:20][CH2:19]1)=[O:17])([CH3:14])([CH3:12])[CH3:13]

참가 물질

8

반응물 5

HCID 176Acetic AcidHCID 10340Sodium CarbonateHCID 788675-AminoindoleHCID 735900tert-Butyl 4-oxopiperidine-1-carboxylateHCID 5049666Sodium triacetoxyborohydride

생성물 1

HCID 66650318tert-butyl 4-(1H-indol-5-ylamino)piperidine-1-carboxylate수율 125.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6342Acetonitrile용매

실험 절차

5-Aminoindole (100 mg, 0.757 mmol) was dissolved in acetonitrile (2 mL), and the solution was added with 1-(tert-butoxycarbonyl)-4-piperidinone (181 mg, 0.908 mmol), acetic acid (0.870 mL, 15.2 mmol) and sodium triacetoxyborohydride (160 mg, 0.755 mmol) little by little, followed by stirring at room temperature for 1 hour. The reaction mixture was added with water and sodium carbonate to adjust the pH to 9. The mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to obtain 5-[1-(tert-butoxycarbonyl)-4-piperidylamino]indole (300 mg).

후처리

  1. extractionThe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-7553ba8747dd4129bdae1918f61fc2ba
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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