Water → 3-(3,5-Difluorophenyl)-3-methoxy-1-methyl pyrrolidine

HRID 1188161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1188161
[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:14][CH3:15])[CH2:13][CH2:12][NH:11][CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1.O.[CH2:17](OCC)C>C(O)=O.C=O>[F:1][C:2]1[CH:3]=[C:4]([C:9]2([O:14][CH3:15])[CH2:13][CH2:12][N:11]([CH3:17])[CH2:10]2)[CH:5]=[C:6]([F:8])[CH:7]=1

Komponenten

6

Edukt 3

HCID 962WaterHCID 3283Diethyl EtherHCID 199358743-(3,5-Difluorophenyl)-3-methoxypyrrolidine

Produkt 1

HCID 462192243-(3,5-Difluorophenyl)-3-methoxy-1-methyl pyrrolidine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 284Formic AcidLösungsmittelHCID 712FormaldehydeLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of (+)-3-(3,5-difluorophenyl)-3-methoxypyrrolidine (0.02 g, 0.094 mmol) in formic acid (1 ml) and formaldehyde (37% solution in water, 1 ml) was heated at 85° C. for 5 h. The mixture was allowed to reach ambient temperature, water (5 ml) and diethyl ether was added, the phases were separated and the aqueous phase was basified by the addition of aqueous sodium hydroxide (5 M). The aqueous phase was extracted twice with ethyl acetate, the combined organic phases was dried (Na2SO4) and evaporated to give the crude product which was diluted in methanol and analyzed by GCMS. MS m/z (relative intensity, 70 eV) 227 (M+, 5), 212 (29), 197 (25), 141 (42), 57 (bp).

Aufarbeitung

  1. customto reach ambient temperature
  2. customthe phases were separated
  3. additionthe aqueous phase was basified by the addition of aqueous sodium hydroxide (5 M)
  4. extractionThe aqueous phase was extracted twice with ethyl acetate
  5. dry with materialthe combined organic phases was dried (Na2SO4)
  6. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-3ec15ecca22842ee89e30829c5dc9d07
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08673962B2

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