Lithium Hydroxide → 1-Acetyl-6-bromo-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

HRID 401650노트

반응식

HRID 401650 반응식
C[O:2][C:3]([CH:5]1[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([Br:15])[CH:11]=2)[N:6]1[C:16](=[O:18])[CH3:17])=[O:4].[Li+].[OH-]>C1COCC1.CO.O>[C:16]([N:6]1[C:7]2[C:12](=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=2)[CH2:13][CH2:14][CH:5]1[C:3]([OH:4])=[O:2])(=[O:18])[CH3:17]

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 596259921-Acetyl-6-bromo-1,2,3,4-tetrahydro-quinoline-2-carboxylic acid methyl ester

생성물 1

HCID 596259471-Acetyl-6-bromo-1,2,3,4-tetrahydroquinoline-2-carboxylic acid

시약·촉매·용매 1

HCID 21892291Methanol tetrahydrofuran water용매

실험 절차

To a solution of compound 25b (116 mg, 0.37 mmol) in THF/MeOH/H2O (2/2/2 mL) was added LiOH (62 mg, 1.48 mmol). The reaction mixture was stirred at room temperature for 3 h. The resultant mixture was concentrated under reduced pressure, partitioned between CH2Cl2 and H2O, and the aqueous phase was brought to pH 5 by the addition of 2N HCl (aq). The organic phase was dried over Na2SO4, filtered, and concentrated under reduced pressure to give the crude compound 25c, which was used in the next step without further purification. LC/MS m/z 298.0 (M+H+), 300.0 (M+2H+).

후처리

  1. concentrationThe resultant mixture was concentrated under reduced pressure
  2. custompartitioned between CH2Cl2 and H2O
  3. additionthe aqueous phase was brought to pH 5 by the addition of 2N HCl (aq)
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-23d2c8b03159411bbe5062b878a78be3
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08741887B2

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