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

HRID 405804ノート

反応式

HRID 405804 の反応式
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

参加物

8

反応物 5

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21892291Methanol tetrahydrofuran water溶媒

反応条件

温度
90 °C

実験手順

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)+.

後処理

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

出典と根拠

ORDレコード
ord-410d96b87ba142b4925751567c93760b
出典データセット
uspto-grants-2014_06
特許番号
US08754071B2

反応ノート

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