Trifluoroacetic acid → L-Proline, 1-ethyl-5-oxo-

HRID 554084Notes

Reaction equation

HRID 554084 reaction equation
[CH2:1]([N:3]1[C:14](=[O:15])[CH2:13][CH2:12][C@H:4]1[C:5]([O:7]C(C)(C)C)=[O:6])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[CH2:1]([N:3]1[C:14](=[O:15])[CH2:13][CH2:12][C@H:4]1[C:5]([OH:7])=[O:6])[CH3:2]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 674618121,1-Dimethylethyl 1-ethyl-5-oxo-prolinate

Product 1

HCID 18605196L-Proline, 1-ethyl-5-oxo-Yield 132.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,1-Dimethylethyl 1-ethyl-5-oxoprolinate (0.933 g) was dissolved in dichloromethane (˜5 ml) and treated with trifluoroacetic acid (1 ml). The mixture was stirred for 3 hrs at room temperature and then evaporated. The residue was taken up in toluene and evaporated once more. This gave partially pure (>95%) 1-ethyl-5-oxo-proline as an orange/yellow oil (0.914 g) which was used without further purification.

Workup

  1. customevaporated
  2. customevaporated once more

Sources & evidence

ORD record
ord-0dd33b2c48a249e7bb248ca6f596ab4b
Source dataset
uspto-grants-2011_11
Patent number
US08048907B2

Reaction notes

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