Borane;tetrahydrofuran → Tert-butyl 3-((pyridin-3-ylamino)methyl)piperazine-1-carboxylate

HRID 549770

반응식

HRID 549770 반응식
B.C1COCC1.[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][C:14]([CH:16]2[NH:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)=O)[CH:8]=1>C1COCC1>[N:7]1[CH:12]=[CH:11][CH:10]=[C:9]([NH:13][CH2:14][CH:16]2[NH:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)[CH:8]=1

참가 물질

4

반응물 2

HCID 2723981Borane;tetrahydrofuranHCID 59671553Tert-butyl 3-(pyridin-3-ylcarbamoyl)piperazine-1-carboxylate

생성물 1

HCID 59671589Tert-butyl 3-((pyridin-3-ylamino)methyl)piperazine-1-carboxylate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Borane-THF complex (1.0 M solution in THF, 3.4 mL, 3.4 mmol) was added to a solution of tert-butyl 3-(pyridin-3-ylcarbamoyl)piperazine-1-carboxylate (522 mg, 1.70 mmol) in THF (4 mL). The reaction mixture was heated to reflux for 5 h. Upon cooling to rt, the reaction mixture was carefully quenched by the dropwise addition of MeOH. After gas evolution ceased, MeOH (10 mL) was added, and the reaction mixture was heated to reflux overnight. Upon cooling to rt, the reaction mixture was concentrated under reduced pressure, yielding the title compound which was used without further purification. LC-MS: RT=2.90 min, [M+H]+=293.1.

후처리

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 5 h
  3. customthe reaction mixture was carefully quenched by the dropwise addition of MeOH
  4. additionMeOH (10 mL) was added
  5. temperaturethe reaction mixture was heated
  6. temperatureto reflux overnight
  7. temperatureUpon cooling to rt
  8. concentrationthe reaction mixture was concentrated under reduced pressure

출처 및 근거

ORD 기록
ord-2134e578d1b34acb8e02faf082894561
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07943622B2

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