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

HRID 570321

반응식

HRID 570321 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-a5e09d88d38c468ea5828ae0f5375f94
출처 데이터셋
uspto-grants-2015_05
특허 번호
US09023839B2

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