(Hexahydro-1H-pyrrolizin-7A-YL)methanamine → 5-{[(3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-yl)amino]methyl}-1-azabicyclo[3.3.0]octane

HRID 1645936Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1645936
Br[CH2:2][CH:3]=[C:4]([CH3:51])[CH2:5][CH2:6][CH:7]=[C:8]([CH3:50])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:49])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:48])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:47])[CH2:21][CH2:22][CH:23]=[C:24]([CH3:46])[CH2:25][CH2:26][CH:27]=[C:28]([CH3:45])[CH2:29][CH2:30][CH:31]=[C:32]([CH3:44])[CH2:33][CH2:34][CH:35]=[C:36]([CH3:43])[CH2:37][CH2:38][CH:39]=[C:40]([CH3:42])[CH3:41].[NH2:52][CH2:53][C:54]12[CH2:61][CH2:60][CH2:59][N:58]1[CH2:57][CH2:56][CH2:55]2>C1C=CC=CC=1>[CH3:51][C:4]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:50])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:49])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:48])[CH2:17][CH2:18][CH:19]=[C:20]([CH3:47])[CH2:21][CH2:22][CH:23]=[C:24]([CH3:46])[CH2:25][CH2:26][CH:27]=[C:28]([CH3:45])[CH2:29][CH2:30][CH:31]=[C:32]([CH3:44])[CH2:33][CH2:34][CH:35]=[C:36]([CH3:43])[CH2:37][CH2:38][CH:39]=[C:40]([CH3:42])[CH3:41])=[CH:3][CH2:2][NH:52][CH2:53][C:54]12[CH2:61][CH2:60][CH2:59][N:58]1[CH2:57][CH2:56][CH2:55]2

Komponenten

4

Edukt 2

HCID 10654304(Hexahydro-1H-pyrrolizin-7A-YL)methanamineHCID 543963751-Bromo-3,7,11,15,19,23,27,31,35,39-decamethyltetraconta-2,6,10,14,18,22,26,30,34,38-decaene

Produkt 1

HCID 539502095-{[(3,7,11,15,19,23,27,31,35,39-Decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaen-1-yl)amino]methyl}-1-azabicyclo[3.3.0]octaneAusbeute 51,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Under an atmosphere of argon, a solution of 1-bromo-3,7,11,15,19,23,27,31,35,39-decamethyl-2,6,10,14,18,22,26,30,34,38-tetracontadecaene [8.00 g, 10.5 mmol, prepared as described in Example 4-a)] in 48.0 ml of benzene was added in dropwise to a solution of 5-aminomethyl-1-azabicyclo-[3.3.0]octane (1.76 g, 12.6 mmol) in 48.0 ml of benzene at 15° C. and the resulting solution was stirred at 50° C. for 5 hours. The solvent in the reaction mixture was evaporated in vacuo to dryness and the remaining residue was partitioned between chloroform and 10% sodium hydroxide aqueous solution. The organic layer was washed with saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, filtered and evaporated in vacuo to dryness to give a brown residue. The residue was chromatographed on silica gel, eluting with CH2Cl2 /MeOH (10.0:0-10:1.5) to afford 4.4 g (51.1%) of the desired compound, as colorless crystals.

Aufarbeitung

  1. customThe solvent in the reaction mixture was evaporated in vacuo to dryness
  2. customthe remaining residue was partitioned between chloroform and 10% sodium hydroxide aqueous solution
  3. washThe organic layer was washed with saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo to dryness
  7. customto give a brown residue
  8. customThe residue was chromatographed on silica gel
  9. washeluting with CH2Cl2 /MeOH (10.0:0-10:1.5)

Quellen und Nachweise

ORD-Eintrag
ord-46666d6dd12f4e1b92d80443aa08119d
Quelldatensatz
uspto-grants-1993_01
Patentnummer
US05177102

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