Reaction #84050

ord-b3b1aaa0e07f4281b55d14c723e1b6a1

Reaction equation

Oc1c(F)c(F)c(F)c(F)c1F
pentafluorophenol
ClCCCl
EDC
Cl.O=C(O)CC1CN2CCC1CC2
1-azabicyclo[2.2.2]oct-3-ylacetic acid hydrochloride
Cl.O=C(CC1CN2CCC1CC2)Oc1c(F)c(F)c(F)c(F)c1F
Pentafluorophenyl (1-azabicyclo[2.2.2]oct-3-yl)acetate hydrochloride

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    ConcentrationThe contents of the flask are concentrated in vacuo
  2. 2
    Otherdried under high vacuum
  3. 3
    OtherThe resulting crude product is employed without further purification in the following stages

Procedure

358 mg (1.94 mmol) of pentafluorophenol, 120.5 mg (0.63 mmol) of EDC and 1 drop of N,N-diisopropylethylamine are added to a solution of 100 mg (0.49 mmol) of 1-azabicyclo[2.2.2]oct-3-ylacetic acid hydrochloride in 4 ml of dichloromethane at 0° C. The mixture is stirred at room temperature for 18 h. The contents of the flask are concentrated in vacuo and dried under high vacuum. The resulting crude product is employed without further purification in the following stages.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09433614B2uspto-grants-2016_09