Azacycloundecan-2-one → 2-Methoxyazacyclododec-1-ene

HRID 2054564

Reaction equation

HRID 2054564 reaction equation
[C:1]1(=O)[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][NH:2]1.F[B-](F)(F)F.[CH3:18][O+:19]([CH3:21])C.C(=O)(O)[O-].[Na+]>C(Cl)Cl>[CH3:18][O:19][C:21]1[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:1][N:2]=1

Participants

5

Reactant 3

HCID 70523Azacycloundecan-2-oneHCID 516892Sodium BicarbonateHCID 2735153Oxonium, trimethyl-, tetrafluoroborate(1-) (1:1)

Product 1

HCID 129577422-Methoxyazacyclododec-1-ene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-Azacycloundecanone (0.87 g) was dissolved in 20 mL methylene chloride and stirred at room temperature under nitrogen. 1.5 g Trimethyloxonium tetrafluoroborate was added and the reaction stirred overnight. The mixture was added to saturated aqueous sodium bicarbonate and extracted with methylene chloride (2×). The combined organic layers were washed with brine, dried over magnesium sulfate, and the solvent evaporated to provide crude 2-methoxyazacyclododec-1-ene.

Workup

  1. stirringthe reaction stirred overnight
  2. extractionextracted with methylene chloride (2×)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent evaporated

Sources & evidence

ORD record
ord-ebd9a9e795624384900e488e399f1f20
Source dataset
uspto-grants-2008_02
Patent number
US07329683B2

Linked notes

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