Ethyl 6,6,6-trifluoro-3-(nitromethyl)hexanoate → 4-(3,3,3-Trifluoropropyl)pyrrolidin-2-one

HRID 69555Notes

Reaction equation

HRID 69555 reaction equation
[F:1][C:2]([F:17])([F:16])[CH2:3][CH2:4][CH:5]([CH2:12][N+:13]([O-])=O)[CH2:6][C:7](OCC)=[O:8]>[Ni].C(O)C>[F:1][C:2]([F:17])([F:16])[CH2:3][CH2:4][CH:5]1[CH2:12][NH:13][C:7](=[O:8])[CH2:6]1

Participants

4

Reactant 1

HCID 86671451Ethyl 6,6,6-trifluoro-3-(nitromethyl)hexanoate

Product 1

HCID 179489644-(3,3,3-Trifluoropropyl)pyrrolidin-2-oneYield 97.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

A mixture of crude ethyl 6,6,6-trifluoro-3-(nitromethyl)hexanoate a7 (50 g), Raney Nickel (570 mg, 9.7 mmol, 0.05 eq) and Vanadium metavanadate (227 mg, 2 mmol, 0.01 eq) in ethanol (1 l) is placed in an autoclave under hydrogen pressure (50 bars) at 50° C. for 40 h. After cooling, filtration over celite and condensation under vacuum, 4-(3,3,3-trifluoropropyl)pyrrolidin-2-one a8 (34.3 g) is isolated.

Workup

  1. customat 50° C.
  2. customfor 40 h
  3. temperatureAfter cooling
  4. filtrationfiltration
  5. customover celite and condensation under vacuum

Sources & evidence

ORD record
ord-9849900a2ba5488ead38c4e729a8e0ec
Source dataset
uspto-grants-2014_09
Patent number
US08822508B2

Reaction notes

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