Lithium Hydroxide → 2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetic Acid

HRID 1091725노트

반응식

HRID 1091725 반응식
[OH-].[Li+].[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([O:13]CC)=[O:12])=[CH:6][C:5]=1[C:16]([N:18]1[CH2:23][CH2:22][CH:21]([O:24][CH3:25])[CH2:20][CH2:19]1)=[O:17]>C1COCC1.O>[F:3][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][C:11]([OH:13])=[O:12])=[CH:6][C:5]=1[C:16]([N:18]1[CH2:19][CH2:20][CH:21]([O:24][CH3:25])[CH2:22][CH2:23]1)=[O:17]

참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 57791780Ethyl 2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetate

생성물 1

HCID 577917632-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetic Acid수율 85.2%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

Lithium hydroxide (0.752 g, 31.39 mmol) was added in one portion to ethyl 2-(4-fluoro-3-(4-methoxypiperidine-1-carbonyl)phenyl)acetate (42) (2.03 g, 6.28 mmol) in THF (20 mL) and water (20 ml) at 25° C. under air. The resulting mixture was stirred at room temperature for 2 hours. The THF was evaporated and the mixture diluted with water (30 mL). The aqueous solution was acidified with 2N HCl and the product extracted into EtOAc (3×30 ml). The combined extracts were dried (MgSO4), filtered and evaporated to a give the desired material as a white solid (1.580 g, 85% yield); 1H NMR (400.132 MHz, CDCl3) δ 1.54-1.84 (3H, m), 1.89-1.96 (1H, m), 3.12-3.20 (1H, m), 3.36 (3H, s), 3.45-3.53 (2H, m), 3.58 (2H, s), 3.60-3.66 (1H, m), 3.93-4.02 (1H, m), 7.01-7.06 (1H, m), 7.28-7.32 (2H, m); m/z (LC-MS, ESI+), RT=0.78 (M+H 296.3).

후처리

  1. customThe THF was evaporated
  2. additionthe mixture diluted with water (30 mL)
  3. extractionthe product extracted into EtOAc (3×30 ml)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. filtrationfiltered
  6. customevaporated to

출처 및 근거

ORD 기록
ord-df80415fb7fa4722abc38a79dda1f609
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129380B2

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