Acetonitrile → Trifluoroacetic acid

HRID 1752022ノート

反応式

HRID 1752022 の反応式
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][O:21]S(C2C=CC(C)=CC=2)(=O)=O)[CH2:10][CH2:9]1)=O)(C)(C)C.CC#N.C([O-])([O-])=O.[K+].[K+].[F:41][C:42]1[CH:47]=[C:46]([F:48])[CH:45]=[C:44]([F:49])[C:43]=1O.[C:51]([OH:57])([C:53]([F:56])([F:55])[F:54])=[O:52]>CC(O)=O.O>[F:41][C:42]1[CH:47]=[C:46]([F:48])[CH:45]=[C:44]([F:49])[C:43]=1[O:21][CH2:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH:11]1[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]1.[C:51]([OH:57])([C:53]([F:56])([F:55])[F:54])=[O:52]

参加物

8

反応物 5

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 11430Potassium CarbonateHCID 5199742,4,6-TrifluorophenolHCID 462129884-[2-(Toluene-4-sulfonyloxymethyl)phenyl]piperidine-1-carboxylic acid t-butyl ester

生成物 2

HCID 6422Trifluoroacetic acid収率 242.6%HCID 46189893Ampreloxetine

試薬・触媒・溶媒 1

HCID 21899381Acetic acid--water (1/1)溶媒

反応条件

温度
50 °C

実験手順

4-[2-(Toluene-4-sulfonyloxymethyl)phenyl]piperidine-1-carboxylic acid t-butyl ester (2.1 g, 4.7 mmol, 1.0 eq.) was dissolved in MeCN (46 mL, 890 mmol) and added to K2CO3 (1.9 g, 14 mmol, 3.0 eq.) and 2,4,6-trifluorophenol (1.0 g, 7.0 mmol, 1.5 eq.). The mixture was shaken at 50° C. overnight, then cooled to room temperature. The supernatant was separated from the K2CO3 and other solids. TFA (7 mL, 90 mmol, 20.0 eq.) was added to the supernatant and the mixture was shaken overnight at room temperature. The solution was then concentrated to yield a crude residue. The residue was dissolved in 5.0 mL 1:1 AcOH/H2O, then in an additional 2.0 mL AcOH, filtered and purified by preparative HPLC to yield the title compound as a TFA salt (1.3 g, 97.5% purity). MS m/z: [M+H]+ calcd for C18H18F3NO, 322.13. found 322.2.

後処理

  1. temperaturecooled to room temperature
  2. customThe supernatant was separated from the K2CO3 and other solids
  3. stirringthe mixture was shaken overnight at room temperature
  4. concentrationThe solution was then concentrated
  5. customto yield a crude residue
  6. filtrationin an additional 2.0 mL AcOH, filtered
  7. custompurified by preparative HPLC

出典と根拠

ORDレコード
ord-e7663c0568924787aa5e47323cd93c8b
出典データセット
uspto-grants-2015_10
特許番号
US09162982B2

反応ノート

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