Allyl bromide → HCID 18940748, compound

HRID 356075Notes

Reaction equation

HRID 356075 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[CH2:14][CH2:15][N:16]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:17][CH2:18][CH2:19][N:20]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:21][CH2:22][CH2:23][NH:24][C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[H-].[Na+].[CH2:48](Br)[CH:49]=[CH2:50]>CN(C=O)C>[CH2:50]([N:24]([C:25]([O:27][C:28]([CH3:31])([CH3:29])[CH3:30])=[O:26])[CH2:23][CH2:22][CH2:21][N:20]([C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:19][CH2:18][CH2:17][N:16]([CH2:15][CH2:14][CH:9]1[CH2:10][CH2:11][CH2:12][CH2:13][N:8]1[C:1]([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2])[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH:49]=[CH2:48]

Participants

5

Reactant 3

HCID 7841Allyl bromide2×HCID 24758Sodium hydride2×HCID 18940756HCID 18940756, compound

Product 1

HCID 18940748HCID 18940748, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.13 g (1.758 mmol) of 1-[2-[(N-BOC)-2-piperidyl]-ethyl]-1,5,9-tri-BOC-1,5,9-triazanonane in 11.3 ml of DMF there are added, with stirring, 0.14 g (3.5 mmol) of sodium hydride dispersion (approximately 60%) and, after 10 minutes, 0.296 ml (3.5 mmol) of allyl bromide (Fluka, Buchs, Switzerland). The reaction mixture is stirred at room temperature for 15 hours and then a further 1/3 of the original amount of sodium hydride dispersion (approximately 60%) and a further 1/3 of the original amount of allyl bromide are added, the reaction mixture is stirred at room temperature for a further 24 hours and is then concentrated by evaporation in vacuo. The residue is partitioned between water and methylene chloride, and the organic phase is washed with brine, dried over sodium sulfate and concentrated by evaporation. After purification of the residue by flash chromatography on silica gel having a particle size of 0.04-0.063 mm using a hexane/tert-butyl methyl ether mixture (7:3), the title compound is obtained in the form of a resin, Rf value=0.34 (silica gel/methylene chloride:methanol (30:1)).

Workup

  1. stirringThe reaction mixture is stirred at room temperature for 15 hours
  2. stirringthe reaction mixture is stirred at room temperature for a further 24 hours
  3. concentrationis then concentrated by evaporation in vacuo
  4. customThe residue is partitioned between water and methylene chloride
  5. washthe organic phase is washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated by evaporation
  8. customAfter purification of the residue by flash chromatography on silica gel having a particle size of 0.04-0.063 mm

Sources & evidence

ORD record
ord-e13f35adfd474241a3f73212c065300a
Source dataset
uspto-grants-1998_11
Patent number
US05834486

Reaction notes

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