tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylate → HCID 67225102, 화합물

HRID 1627089노트

반응식

HRID 1627089 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][CH2:24][CH:25]1[CH2:29][CH2:28][N:27]([C:30]([O:32][C:33]([CH3:36])([CH3:35])[CH3:34])=[O:31])[CH2:26]1.C([BH3-])#N.[Na+]>CO.CC(O)=O>[C:33]([O:32][C:30]([N:27]1[CH2:28][CH2:29][CH:25]([CH2:24][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)[CH2:26]1)=[O:31])([CH3:36])([CH3:35])[CH3:34]

참가 물질

6

반응물 3

HCID 2756485tert-Butyl 3-(aminomethyl)pyrrolidine-1-carboxylateHCID 5003444Sodium cyanoborohydrideHCID 582935211-tert-Butyl 4-methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate

생성물 1

HCID 67225102HCID 67225102, 화합물수율 85.3%

시약·촉매·용매 2

HCID 176Acetic Acid촉매HCID 887Methanol용매

실험 절차

To a solution of 1-tert-butyl 4-methyl 3-formyl-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate (91 mg, 0.3 mmol) in MeOH (2 mL) was added AcOH (5 drops) and tert-butyl 3-(aminomethyl)pyrrolidine-1-carboxylate (90 mg, 0.45 mmol). After stirring for 60 min at rt, the reaction mixture was cooled to 0° C. Sodium cyanoborohydride (57 mg, 0.9 mmol) was added, and the reaction mixture was stirred for an additional 3 h at rt. The mixture was quenched with water and extracted with ethyl acetate. The combined organic layers washed with saturated NaHCO3 and with brine, dried over Na2SO4, and concentrated in vacuo to give 125 mg of crude 1-tert-butyl 4-methyl 3-(((1-(tert-butoxycarbonyl)pyrrolidin-3-yl)methylamino)methyl)-1H-pyrrolo[2,3-b]pyridine-1,4-dicarboxylate as a colorless oil which was used without further purification. [M+H] found 489.40.

후처리

  1. temperaturethe reaction mixture was cooled to 0° C
  2. stirringthe reaction mixture was stirred for an additional 3 h at rt
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe combined organic layers washed with saturated NaHCO3 and with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-47624b904d794a6cb1e96a8100e78b0e
출처 데이터셋
uspto-grants-2014_07
특허 번호
US08785429B2

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