Water → (R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylate

HRID 931286노트

반응식

HRID 931286 반응식
Cl.[NH:2]1[CH2:7][CH2:6][CH2:5][C@@H:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3]1.C(N(CC)CC)C.Cl[C:21]1[N:26]=[C:25]([NH2:27])[C:24]([N+:28]([O-:30])=[O:29])=[CH:23][CH:22]=1.O>C(#N)C>[NH2:27][C:25]1[N:26]=[C:21]([N:2]2[CH2:7][CH2:6][CH2:5][C@@H:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])[CH2:3]2)[CH:22]=[CH:23][C:24]=1[N+:28]([O-:30])=[O:29]

참가 물질

6

반응물 4

HCID 962WaterHCID 8471TriethylamineHCID 27240356-Chloro-3-nitropyridin-2-ylamineHCID 44828658Ethyl (3R)-piperidine-3-carboxylate--hydrogen chloride (1/1)

생성물 1

HCID 131735158(R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylate수율 86.7%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of (R)-ethyl piperidine-3-carboxylate hydrochloride salt (1.2 g, 6.21 mmol) in acetonitrile (20 mL) was added triethylamine (2.61 mL, 18.64 mmol). The mixture was stirred for 10 min at room temperature. 6-Chloro-3-nitropyridin-2-amine (753 mg, 4.31 mmol) was added and the reaction mixture was stirred at 80° C. for 3 h. The mixture was cooled to room temperature and water was added. The mixture was extracted with ethyl acetate. The organics were dried over sodium sulfate, filtered and concentrated under reduced pressure to afford (R)-ethyl 1-(6-amino-5-nitropyridin-2-yl)piperidine-3-carboxylate (1.1 g). MS (ES+APCI) (M+H) 295.2.

후처리

  1. stirringthe reaction mixture was stirred at 80° C. for 3 h
  2. temperatureThe mixture was cooled to room temperature
  3. extractionThe mixture was extracted with ethyl acetate
  4. dry with materialThe organics were dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-9e9b6fb66f384ac4bceba6c7f527ff8c
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296745B2

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