Methyl triflate → 5-Methoxy-4-azatricyclo[4.3.1.1,3,8]undec-4-ene

HRID 913050Notes

Reaction equation

HRID 913050 reaction equation
[CH:1]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][CH:3]([NH:4][C:5]3=[O:12])[CH2:2]1)[CH2:9]2.O(C)S([C:17](F)(F)F)(=O)=O>C(Cl)Cl>[CH3:17][O:12][C:5]1[CH:6]2[CH2:11][CH:1]3[CH2:9][CH:8]([CH2:10][CH:3]([CH2:2]3)[N:4]=1)[CH2:7]2

Participants

4

Reactant 2

HCID 9526Methyl triflateHCID 2866474-Azatricyclo[4.3.1.13,8]undecan-5-one

Product 1

HCID 866090545-Methoxy-4-azatricyclo[4.3.1.1,3,8]undec-4-ene

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-azatricyclo[4.3.1.13,8]undecan-5-one 3-A (1.00 g, 6.05 mmol) in 10 mL methylene chloride was added methyl triflate (2.98 g, 3 eq) and the reaction was heated at reflux for 20 min, after which time all volatiles were removed under reduced pressure to afford crude 5-methoxy-4-azatricyclo[4.3.1.13,8]undec-4-ene 3-B which was used in the next step without further purification.

Workup

  1. temperaturethe reaction was heated
  2. temperatureat reflux for 20 min
  3. customafter which time all volatiles were removed under reduced pressure

Sources & evidence

ORD record
ord-f4452dc3a9414858b90eaa30610000e8
Source dataset
uspto-grants-2011_09
Patent number
US08026264B2

Reaction notes

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