(Hexahydro-1H-pyrrolizin-7A-YL)methanamine → 5-{[(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-yl)amino]methyl}-1-azabicyclo[3.3.0]octane

HRID 1645937Notes

Reaction equation

HRID 1645937 reaction equation
Br[CH2:2][CH:3]=[C:4]([CH3:21])[CH2:5][CH2:6][CH:7]=[C:8]([CH3:20])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17].[NH2:22][CH2:23][C:24]12[CH2:31][CH2:30][CH2:29][N:28]1[CH2:27][CH2:26][CH2:25]2>C(O)C>[CH3:21][C:4]([CH2:5][CH2:6][CH:7]=[C:8]([CH3:20])[CH2:9][CH2:10][CH:11]=[C:12]([CH3:19])[CH2:13][CH2:14][CH:15]=[C:16]([CH3:18])[CH3:17])=[CH:3][CH2:2][NH:22][CH2:23][C:24]12[CH2:31][CH2:30][CH2:29][N:28]1[CH2:27][CH2:26][CH2:25]2

Participants

4

Reactant 2

HCID 10654304(Hexahydro-1H-pyrrolizin-7A-YL)methanamineHCID 545679811-Bromo-3,7,11,15-tetramethylhexadeca-2,6,10,14-tetraene

Product 1

HCID 540447775-{[(3,7,11,15-Tetramethyl-2,6,10,14-hexadecatetraen-1-yl)amino]methyl}-1-azabicyclo[3.3.0]octaneYield 49.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Under an atmosphere of argon, a solution of 1-bromo-3,7,11,15-tetramethyl-2,6,10,14-hexadecatetraene [6.90 g, 19.5 mmol, prepared as described in Example 5-a)] in 138 ml of ethanol was added in dropwise to a solution of 5-aminomethyl-1-azabicyclo[3.3.0]octane (3.3 g, 23.6 mmol) in 35 ml of ethanol at the temperature below 0° C. The reaction mixture was allowed to warm slowly from 0°-20° C. and then stirred at 20°-25° C. for 5 hours. The resulting solution was treated as described in Example 8 to afford 4.0 g (49.8%) of the desired compound, as a pale brown oil.

Workup

  1. temperatureto warm slowly from 0°-20° C.
  2. additionThe resulting solution was treated

Sources & evidence

ORD record
ord-b7047e4c52d34b3d8b1685ee31d002b8
Source dataset
uspto-grants-1993_01
Patent number
US05177102

Reaction notes

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