Carbon Dioxide → N,N-diethyl-1-(phenylmethyl)-3-pyrrolidinemethanamine

HRID 980745Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 980745
O=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH:4]([C:14](O)=O)[CH2:3]1.C[N:18]1[CH2:23][CH2:22]O[CH2:20][CH2:19]1.ClC(OCC)=O.C(NCC)C.C(=O)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>ClCCl.O1CCCC1>[CH2:19]([N:18]([CH2:23][CH3:22])[CH2:14][CH:4]1[CH2:3][CH2:2][N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5]1)[CH3:20]

Komponenten

9

Edukt 6

HCID 280Carbon DioxideHCID 79724-MethylmorpholineHCID 8021Diethylamine2×HCID 10928Ethyl chloroformateHCID 990241-Benzyl-5-oxo-pyrrolidine-3-carboxylic acidHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 14075472N,N-diethyl-1-(phenylmethyl)-3-pyrrolidinemethanamineAusbeute 69,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittel3×HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-25 °C

Versuchsvorschrift

To a solution of 32.9 g (0.15 mole) 5-oxo-1-(phenylmethyl)-3-pyrrolidinecarboxylic acid [J. Org. Chem., 26, 1519 (1961)] and 300 ml of dichloromethane was added 15.2 g (0.15 mole) of N-methylmorpholine. After 15 minutes the solution was cooled to -25° C. and 16.3 g (0.15 mole) of ethyl chloroformate was added. After an additional ten minutes, a solution of 13.5 g (0.18 mole) of diethylamine and 18 ml dichloromethane was added to the reaction. Carbon dioxide was evolved and after 1.5 h another 10 g (0.13 mole) of diethylamine in 10 ml of dichloromethane was added. The reaction was stirred four hours, washed with 1N sodium hydroxide, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was added to a suspension of 17.4 g (0.46 mole) of lithium aluminum hydride and 210 ml anhydrous tetrahydrofuran. The reaction was refluxed overnight then cooled to room temperature. The cooled solution was quenched with 17.4 ml water, 17.4 ml 15% sodium hydroxide, and 52.2 ml water. The resulting precipitate was filtered and washed with ethyl alcohol. The filtrate was concentrated under reduced pressure, taken up in dichloromethane, dried over magnesium sulfate. The solvent was removed under vacuum giving 25.8 g (69%) of N,N-diethyl-1-(phenylmethyl)-3-pyrrolidinemethanamine as a yellow oil. This material was used in the next step without purification.

Aufarbeitung

  1. waitAfter an additional ten minutes
  2. washwashed with 1N sodium hydroxide
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. temperatureThe reaction was refluxed overnight
  6. temperaturethen cooled to room temperature
  7. customThe cooled solution was quenched with 17.4 ml water, 17.4 ml 15% sodium hydroxide, and 52.2 ml water
  8. filtrationThe resulting precipitate was filtered
  9. washwashed with ethyl alcohol
  10. concentrationThe filtrate was concentrated under reduced pressure
  11. dry with materialdried over magnesium sulfate
  12. customThe solvent was removed under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-9b25b21de4984043881c81c4fb637e0a
Quelldatensatz
uspto-grants-1987_01
Patentnummer
US04638067

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