Trifluoroacetic acid → HCID 54461475, compound

HRID 2258604Notes

Reaction equation

HRID 2258604 reaction equation
[C:1]([N:4]1[CH:8](O)[CH2:7][CH:6]([CH2:10][CH3:11])[C:5]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:3])[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:1]([N:4]1[CH2:8][CH2:7][CH:6]([CH2:10][CH3:11])[C:5]1([C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 11289610Diethyl 1-Acetyl-5-hydroxy-3-ethylpyrrolidine-2,2-dicarboxylate

Product 1

HCID 54461475HCID 54461475, compoundYield 137.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of diethyl 1-acetyl-5-hydroxy-3-ethylpyrrolidine-2,2-dicarboxylate (287 g, 0.95 mol) and triethylsilane (228 mL, 1.43 mol) in CH2Cl2 (3 L) under argon was added trifluoroacetic acid (735 mL, 9.53 mol) dropwise with stirring while maintaining the internal temperature at 25° C. by means of an ice bath. After stirring for 3 h at 23° C., the solution was concentrated in vacuo, the residue diluted with CH2Cl2 (1.5 L), then treated with H2O (1 L) and solid Na2CO3 with vigorous stirring until the solution was basic. The organic layer was separated, dried (Na2SO4), filtered, then concentrated to give the title compound as a yellow oil (373 g) which was used without further purification.

Workup

  1. stirringAfter stirring for 3 h at 23° C.
  2. concentrationthe solution was concentrated in vacuo
  3. additionthe residue diluted with CH2Cl2 (1.5 L)
  4. additiontreated with H2O (1 L) and solid Na2CO3
  5. stirringwith vigorous stirring until the solution
  6. customThe organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-d515496cb4cb4816994e5693cbfa5356
Source dataset
uspto-grants-1997_08
Patent number
US05661161

Reaction notes

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