Trifluoroacetic acid → HCID 11056701, compound

HRID 1099202Notes

Reaction equation

HRID 1099202 reaction equation
[C:1]([N:4]1[CH:8](O)[CH2:7][CH:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:3])[CH3:2].C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[C:1]([N:4]1[CH2:8][CH2:7][CH:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5]1([C:21]([O:23][CH2:24][CH3:25])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 6589632,2-Diethyl 1-acetyl-5-hydroxy-3-phenyl-2,2-pyrrolidinedicarboxylate

Product 1

HCID 11056701HCID 11056701, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of diethyl 1-acetyl-5-hydroxy-3-phenylpyrrolidine-2,2-dicarboxylate (116.0 g, 331 mmol) and triethylsilane (80 ml, 497 mmol) in dichloromethane (675 ml) was added trifluoroacetic acid (254 ml, 3.32 mol) dropwise with stirring over 45 min. The reaction was allowed to stir for 2.5 h at rt and was then concentrated and redissolved in EtOAc. The organics were washed with sat'd sodium bicarbonate, dried over sodium sulfate, filtered, and concentrated in vacuo to yield diethyl 1-acetyl-3-phenylpyrrolidine-2,2-dicarboxylate as an oil (100%).

Workup

  1. stirringto stir for 2.5 h at rt
  2. concentrationwas then concentrated
  3. dissolutionredissolved in EtOAc
  4. washThe organics were washed with sat'd sodium bicarbonate
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7adb26d3ec474856b0550f6b9a4e5dd4
Source dataset
uspto-grants-2012_03
Patent number
US08143405B2

Reaction notes

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