Trifluoroacetic acid → HCID 54167418, compound

HRID 2288037Notes

Reaction equation

HRID 2288037 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([OH:14])[C:10](=[CH:15][CH3:16])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(N(CC)CC)C.[CH:31]1([C:34]([CH:36](Br)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[F:43])=[O:35])[CH2:33][CH2:32]1>C(Cl)Cl>[CH:31]1([C:34]([CH:36]([N:8]2[CH2:13][CH2:12][CH:11]([OH:14])[C:10](=[CH:15][CH3:16])[CH2:9]2)[C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[F:43])=[O:35])[CH2:33][CH2:32]1

Participants

6

Reactant 4

HCID 6422Trifluoroacetic acidHCID 8471TriethylamineHCID 234358712-Bromo-1-cyclopropyl-2-(2-fluorophenyl)ethan-1-oneHCID 545398291,1-Dimethylethyl 3-ethylidene-4-hydroxy-1-piperidinecarboxylate

Product 1

HCID 54167418HCID 54167418, compoundYield 74.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 20 ml of methylene chloride, 1.51 g (6.7 mmol) of 1-(t-butoxycarbonyl)-3-ethylidene-4-hydroxypiperidine were dissolved. To the resulting solution, 5 ml of trifluoroacetic acid were added under ice cooling, followed by stirring at room temperature for 2 hours. To the reaction mixture, 11 ml of triethylamine and 1.70 g (6.7 mmol) of α-cyclopropylcarbonyl-2-fluorobenzylbromide were added under ice cooling, followed by stirring at room temperature for 2 hours. The solvent was distilled off under reduced pressure. Ethyl acetate was added to the residue and the solid so precipitated was filtered off. The filtrate was then concentrated by evaporation under reduced pressure. The residue was subjected to chromatography on a silica gel column (eluting solvent: chloroform/methanol=100/1), whereby 1.52 g (yield: 74.9%) of the title compound were obtained as a yellow oil.

Workup

  1. stirringby stirring at room temperature for 2 hours
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionEthyl acetate was added to the residue
  4. customthe solid so precipitated
  5. filtrationwas filtered off
  6. concentrationThe filtrate was then concentrated by evaporation under reduced pressure
  7. washThe residue was subjected to chromatography on a silica gel column (eluting solvent: chloroform/methanol=100/1)

Sources & evidence

ORD record
ord-b8a61688cc8d4f38a3aa2497c419a0a7
Source dataset
uspto-grants-2000_07
Patent number
US06087379

Reaction notes

Loading…