Hydrochloric Acid → 2-(3,3-Difluoropyrrolidin-1-yl)-3-methoxypropanoic acid

HRID 405804

반응식

HRID 405804 반응식
Br[CH:2]([CH2:7][O:8][CH3:9])[C:3]([O:5]C)=[O:4].[F:10][C:11]1([F:16])[CH2:15][CH2:14][NH:13][CH2:12]1.C([O-])([O-])=O.[K+].[K+].[Li+].[OH-].Cl>CN(C=O)C.C1COCC1.CO.O>[F:10][C:11]1([F:16])[CH2:15][CH2:14][N:13]([CH:2]([CH2:7][O:8][CH3:9])[C:3]([OH:5])=[O:4])[CH2:12]1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 11430Potassium CarbonateHCID 352460Methyl 2-bromo-3-methoxypropanoateHCID 27828273,3-Difluoropyrrolidine

생성물 1

HCID 712812272-(3,3-Difluoropyrrolidin-1-yl)-3-methoxypropanoic acid

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21892291Methanol tetrahydrofuran water용매

반응 조건

온도
90 °C

실험 절차

A mixture of methyl 2-bromo-3-methoxypropanoate (132.0 mg, 0.66 mmol), 3,3-difluoropyrrolidine (70.6 mg, 0.66 mmol) and K2CO3 (91.2 mg, 0.66 mmol) in DMF (2 mL) was heated at 90° C. for 3 hours. The mixture was subjected to standard aqueous workup to afford a residue which was dissolved in THF/MeOH/H2O (3:2:1, 5 mL). LiOH (6N, 3.3 mmol) was added and the resulting mixture was stirred at room temperature for 30 minutes. The solution was acidified to pH5 by addition of 6N HCl. All solvents were removed under vacuum to give a crude 2-(3,3-difluoropyrrolidin-1-yl)-3-methoxypropanoic acid (58) which was used without purification. MS m/z 210.1 (M+1)+.

후처리

  1. customto afford a residue which
  2. customAll solvents were removed under vacuum

출처 및 근거

ORD 기록
ord-410d96b87ba142b4925751567c93760b
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08754071B2

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