Sodium Hydroxide → 6-Bromo-2-pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydro-quinoline

HRID 271683노트

반응식

HRID 271683 반응식
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]([CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH:6]=[CH:5]2.[OH-].[Na+]>C(O)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]([CH2:12][N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:6][CH2:5]2

참가 물질

4

반응물 2

HCID 14798Sodium HydroxideHCID 673647966-Bromo-2-pyrrolidin-1-ylmethyl-quinoline

생성물 1

HCID 673633166-Bromo-2-pyrrolidin-1-ylmethyl-1,2,3,4-tetrahydro-quinoline

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Under an argon atmosphere 0.69 mL (6.87 mmol) borane-pyridine complex are added to a solution of 500 mg (1.72 mmol) 6-bromo-2-pyrrolidin-1-ylmethyl-quinoline (see 3.45b) in 10 mL acetic acid at RT. The mixture is stirred for 7 h at RT, again combined with 0.35 mL (3.46 mmol) borane-pyridine complex and stirred for another hour at RT. It is cooled to 0° C. and the solution is made basic with 8% NaOH solution. The aqueous phase is extracted with EtOAc and the solvent is eliminated i.vac. The residue is taken up with water and acidified with 12% HCl. The aqueous phase is extracted with EtOAc and then made basic with 20% NaOH solution while cooling with ice. The aqueous phase is extracted with EtOAc. The organic phase is dried over MgSO4 and the solvent is eliminated i.vac.

후처리

  1. stirringstirred for another hour at RT
  2. temperatureIt is cooled to 0° C.
  3. extractionThe aqueous phase is extracted with EtOAc
  4. extractionThe aqueous phase is extracted with EtOAc
  5. temperaturewhile cooling with ice
  6. extractionThe aqueous phase is extracted with EtOAc
  7. dry with materialThe organic phase is dried over MgSO4

출처 및 근거

ORD 기록
ord-10f61431b36d4f5f917a4aa83aa01a03
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452911B2

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