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1-Chloroethyl chloroformate → 2-(S)-(3,5-Dichlorobenzyloxy)-3-(S)-phenylmorpholine

HRID 1683409
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1683409
C([N:8]1[CH2:13][CH2:12][O:11][C@H:10]([O:14][CH2:15][C:16]2[CH:21]=[C:20]([Cl:22])[CH:19]=[C:18]([Cl:23])[CH:17]=2)[C@@H:9]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)C1C=CC=CC=1.ClC(OC(Cl)C)=O>ClCCCl>[Cl:23][C:18]1[CH:17]=[C:16]([CH:21]=[C:20]([Cl:22])[CH:19]=1)[CH2:15][O:14][C@H:10]1[O:11][CH2:12][CH2:13][NH:8][C@H:9]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 5213051-Chloroethyl chloroformateHCID 228607764-benzyl-2-(S)-(3,5-dichlorobenzyloxy)-3-(S)-phenylmorpholine

Produkt 1

HCID 228607442-(S)-(3,5-Dichlorobenzyloxy)-3-(S)-phenylmorpholineAusbeute 20 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

A solution of 0.33 g (0.77 mmole) of 4-benzyl-2-(S)-(3,5-dichlorobenzyloxy)-3-(S)-phenylmorpholine (from Example 44, Step B) and 0.22 g (1.54 mmole) of 1-chloroethyl chloroformate in 4.5 mL of 1,2-dichloroethane was placed in a pressure vial which was lowered into an oil bath which was heated to 110° C. After stirring for 60 hr the solution was cooled and concentrated in vacuo. The residue was dissolved in 7 mL of methanol and the resulting solution was heated at reflux for 30 min. The mixture was cooled and treated with several drops of concentrated aqueous ammonia and the solution was concentrated. The residue was partly purified by flash chromatography on 67 g of silica eluting with 1.5 L of 100:1 methylene chloride: methanol, and the rich cuts were purified by flash chormatography on 32 g of silica eluting with 50:50 hexanes: ethyl acetate and then 50:50:5 hexanes:ethyl acetate:methanol to give 0.051 g (20%) of an oil, which by 1H NMR was pure cis morpholine.

Aufarbeitung

  1. customwas lowered into an oil bath
  2. temperaturewas cooled
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue was dissolved in 7 mL of methanol
  5. temperaturethe resulting solution was heated
  6. temperatureat reflux for 30 min
  7. temperatureThe mixture was cooled
  8. additiontreated with several drops of concentrated aqueous ammonia
  9. concentrationthe solution was concentrated
  10. customThe residue was partly purified by flash chromatography on 67 g of silica eluting with 1.5 L of 100:1 methylene chloride
  11. custommethanol, and the rich cuts were purified by flash chormatography on 32 g of silica eluting with 50:50 hexanes

Quellen und Nachweise

ORD-Eintrag
ord-90fc7405153042cc90ed23af33f37c0e
Quelldatensatz
uspto-grants-1997_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05637699

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