Trifluoroacetic acid → 3-phenyl-2,5-dihydro-1H-pyrrole

HRID 61422Notes

Reaction equation

HRID 61422 reaction equation
O[C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.FC(F)(F)C(O)=O>>[C:14]1([C:2]2[CH2:3][NH:4][CH2:5][CH:6]=2)[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66662569Tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate

Product 1

HCID 30315313-phenyl-2,5-dihydro-1H-pyrrole

Procedure

A mixture of tert-butyl 3-hydroxy-3-phenylpyrrolidine-1-carboxylate (0.36 g, 0.0014 mol) and trifluoroacetic acid (2.0 mL, 0.026 mol) was stirred under nitrogen at room temp for 1 h. The volatile was removed under vacuum and evaporated with toluene twice. The residue was used in next step w/o further purification. LCMS: 146.1 (M+H)+.

Workup

  1. customThe volatile was removed under vacuum
  2. customevaporated with toluene twice
  3. customThe residue was used in next step w/o further purification

Sources & evidence

ORD record
ord-65540827d1b44fe7a0ea409d9c544733
Source dataset
uspto-grants-2016_09
Patent number
US09440958B2

Reaction notes

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