Methanol → HCID 69206248, compound

HRID 1483917Notes

Reaction equation

HRID 1483917 reaction equation
[CH2:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]2[CH:11]=[C:12](OS(C(F)(F)F)(=O)=O)[CH:13]=[CH:14][CH:15]=2)[CH2:6][CH2:5]1)[CH2:2][CH3:3].[CH2:24](N(CC)CC)C.[CH3:31][OH:32].[OH2:33]>CS(C)=O.CC([O-])=O.CC([O-])=O.[Pd+2].C1(P(C2C=CC=CC=2)CCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:31][O:32][C:24](=[O:33])[C:12]1[CH:13]=[CH:14][CH:15]=[C:10]([CH:7]2[CH2:8][CH2:9][N:4]([CH2:1][CH2:2][CH3:3])[CH2:5][CH2:6]2)[CH:11]=1

Participants

8

Reactant 4

HCID 887MethanolHCID 962WaterHCID 8471TriethylamineHCID 12988960HCID 12988960, compound

Product 1

HCID 69206248HCID 69206248, compound

Reagents, catalysts & solvents 3

HCID 812191,3-Bis(diphenylphosphino)propaneCatalystHCID 167845palladium(II) acetateCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of trifluoro-methanesulfonic acid 3-(1-propyl-piperidin-4-yl)-phenyl ester (1.2 g), triethyl amine (0.9 g), MeOH (5.4 ml), Pd(OAc)2 (25 mg) and 1,3-bis(di-phenyl-phosphino)propane (45 mg) in 15 ml DMSO was stirred at room temperature for 15 min. A stream of CO (g) was passed through the solution for 4-5 min., and then the reaction vessel was placed under a sligthly positive pressure of CO (g). The temp was increased to 70° C. After 6 h the reaction was allowed to cool to r.t. Water was then added, and the aqueous solution was extracted with five portions of ethyl acetate and the combined organic phases were dried (MgSO4), and evaporated. The residue was chromathographed on a silica column using MeOH: CH2Cl2 (1:9 (v/v)) as eluent. The fractions containing pure titled compound were collected, and the solvent was removed in vacuum, affording 650 mg of the titled compound. (MS m/z (rel. intensity, 70 eV) 261 (M+, 5), 233 (16), 232 (bp), 161 (5), 70 (20)

Workup

  1. waitA stream of CO (g) was passed through the solution for 4-5 min.
  2. temperatureThe temp was increased to 70° C
  3. waitAfter 6 h the reaction was allowed
  4. temperatureto cool to r.t
  5. extractionthe aqueous solution was extracted with five portions of ethyl acetate
  6. dry with materialthe combined organic phases were dried (MgSO4)
  7. customevaporated
  8. additionThe fractions containing pure titled compound
  9. customwere collected
  10. customthe solvent was removed in vacuum

Sources & evidence

ORD record
ord-44e2c160162d4386acb528a27067388e
Source dataset
uspto-grants-2016_08
Patent number
USRE046117E1

Reaction notes

Loading…