tert-Butyl ((1-benzylpyrrolidin-3-yl)methyl)carbamate → 1-(1-benzylpyrrolidin-3-yl)-N-methylmethanamine

HRID 1295870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1295870
[H-].[H-].[H-].[H-].[Li+].[Al+3].C(O[C:12](=O)[NH:13][CH2:14][CH:15]1[CH2:19][CH2:18][N:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH2:16]1)(C)(C)C>C1COCC1>[CH2:20]([N:17]1[CH2:18][CH2:19][CH:15]([CH2:14][NH:13][CH3:12])[CH2:16]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Komponenten

4

Edukt 2

HCID 5108694tert-Butyl ((1-benzylpyrrolidin-3-yl)methyl)carbamateHCID 21226445Aluminium lithium hydride

Produkt 1

HCID 46608321-(1-benzylpyrrolidin-3-yl)-N-methylmethanamineAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
-5 °C

Versuchsvorschrift

To a cooled (−5° C.) and stirred solution of LAH (1 M, 7.6 ml) in dry THF (75 ml) was added a solution of (1-benzyl-pyrrolidin-3-ylmethyl)-carbamic acid tert-butyl ester (1.47 g, 5.06 mmol) in THF (22 ml) over 20 minutes. The mixture was then heated at reflux for 2.5 hrs and cooled to room temperature and quenched by successive addition of ethyl acetate (50 ml). The organic layer was then washed with water (2×), 10% NaOH and brine, dried and evaporated to give the desired product in 90% yield.

Aufarbeitung

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 2.5 hrs
  3. temperaturecooled to room temperature
  4. customquenched by successive addition of ethyl acetate (50 ml)
  5. washThe organic layer was then washed with water (2×), 10% NaOH and brine
  6. customdried
  7. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-26bde80f474c4806bddca5de0ac9e020
Quelldatensatz
uspto-grants-2007_07
Patentnummer
US07244758B2

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