(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 1645936Notes

Reaction equation

HRID 1645936 reaction equation
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

Participants

4

Reactant 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

Product 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]octaneYield 51.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Conditions

Temperature
50 °C

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-46666d6dd12f4e1b92d80443aa08119d
Source dataset
uspto-grants-1993_01
Patent number
US05177102

Reaction notes

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