Acetonitrile → Trifluoroacetic acid

HRID 1752022노트

반응식

HRID 1752022 반응식
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]

참가 물질

8

반응물 5

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

생성물 2

HCID 6422Trifluoroacetic acid수율 242.6%HCID 46189893Ampreloxetine

시약·촉매·용매 1

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

반응 조건

온도
50 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e7663c0568924787aa5e47323cd93c8b
출처 데이터셋
uspto-grants-2015_10
특허 번호
US09162982B2

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