Lithium hydroxide, monohydrate → (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid

HRID 59887

반응식

HRID 59887 반응식
[CH2:1]([O:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:18]=[CH:17][C:16]([C:19]([O:21]CC)=[O:20])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2].O[Li].O>C1COCC1.O>[CH2:1]([O:3][C:4]1[CH:27]=[CH:26][CH:25]=[CH:24][C:5]=1[O:6][C@@H:7]1[CH2:12][CH2:11][CH2:10][N:9]([C:13]2[N:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][N:14]=2)[CH2:8]1)[CH3:2]

참가 물질

4

반응물 2

HCID 168937Lithium hydroxide, monohydrateHCID 131737069ethyl (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylate

생성물 1

HCID 118366221(R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid수율 78.5%

시약·촉매·용매 1

HCID 21881883Oxolane--water (1/1)용매

반응 조건

온도
22.5 °C

실험 절차

To a solution of ethyl (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylate (71.5 g, 193 mmol) in THF/H2O (1:1, 2 L) was added LiOH.H2O (24.2 g, 578 mmol) at 20-25° C. The reaction mixture was stirred at 20-25° C. for 24 hours. The mixture was concentrated, and the aqueous phase was washed with diethyl ether (2 times with 500 mL). The aqueous phase was acidified to pH 2 with 1N HCl (˜400 mL). The precipitated solid was filtered and dried to afford (R)-2-(3-(2-ethoxyphenoxy)piperidin-1-yl)pyrimidine-5-carboxylic acid (52 g, 78%). MS (ES+) 344.18 (M+H).

후처리

  1. concentrationThe mixture was concentrated
  2. washthe aqueous phase was washed with diethyl ether (2 times with 500 mL)
  3. filtrationThe precipitated solid was filtered
  4. customdried

출처 및 근거

ORD 기록
ord-7920f8588bf448158309a362e6ad18eb
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09440949B2

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