Ethylene Glycol → HCID 18723484, compound

HRID 2296830Notes

Reaction equation

HRID 2296830 reaction equation
[CH2:1]([N:8]1[CH2:12][CH:11]([CH:13]=[O:14])[CH:10]([CH2:15][N:16]2[CH2:21][CH2:20][CH:19]([C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:18][CH2:17]2)[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:29]([OH:32])[CH2:30]O.[CH3:33][C:34]1C=CC(S(O)(=O)=O)=[CH:38][CH:39]=1.[OH2:44]>C1C=CC=CC=1.CCOCC>[C:2]1([C:1]([N:8]2[CH2:12][CH:11]([CH:13]3[O:32][CH2:29][CH2:30][O:14]3)[CH:10]([CH2:15][N:16]3[CH2:17][CH2:18][CH:19]([C:22]4[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=4)[CH2:20][CH2:21]3)[CH2:9]2)=[O:44])[C:7]2[C:6](=[CH:33][CH:34]=[CH:39][CH:38]=2)[CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 174Ethylene GlycolHCID 521998p-Toluenesulfonic acid monohydrateHCID 18723470HCID 18723470, compound

Product 1

HCID 18723484HCID 18723484, compound

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 3283Diethyl EtherSolvent

Procedure

A solution of 0.046 g (0.104 mmol) of 1-benzyl-3-(RS)-(4-(4-fluorophenyl)piperidinylmethyl)-4-(SR)-formylpyrrolidine, 0.058 mL (1.04 mmol) of ethyleneglycol and 0.047 g (0.25 mmol) of TsOH.H2O in 5 mL of benzene was heated at reflux for 2 h. The reaction mixture was cooled to rt and diluted with ether. The reaction mixture was washed twice with sat'd NaHCO3 solution, dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by chromatography (silica, MeOH:CH2Cl2, 5:95) to give the title compound.

Workup

  1. temperatureat reflux for 2 h
  2. washThe reaction mixture was washed twice with sat'd NaHCO3 solution
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography (silica, MeOH:CH2Cl2, 5:95)

Sources & evidence

ORD record
ord-41ca63f7e78446b39f394d7e0e25b181
Source dataset
uspto-grants-2002_12
Patent number
US06489354B1

Reaction notes

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