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

HRID 557937Notes

Reaction equation

HRID 557937 reaction equation
O[C:2]1([C:14]([CH3:16])=[CH2:15])[CH2:6][CH2:5][N:4](C(OC(C)(C)C)=O)[CH2:3]1.[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20].[Al]>>[F:17][C:18]([F:23])([F:22])[C:19]([OH:21])=[O:20].[C:14]([C:2]1[CH2:3][NH:4][CH2:5][CH:6]=1)([CH3:16])=[CH2:15]

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5359268AluminumHCID 66661850Tert-butyl 3-hydroxy-3-isopropenylpyrrolidine-1-carboxylate

Product 1

HCID 666625073-isopropenyl-2,5-dihydro-1H-pyrrole trifluoroacetate

Procedure

tert-Butyl 3-hydroxy-3-isopropenylpyrrolidine-1-carboxylate (1.51 g, 0.00664 mol) was dissolved in trifluoroacetic acid (10.0 mL, 0.130 mol) under N2 at rt. The reaction flask was wrapped with aluminum foil and the mixture was stirred overnight. The reaction mixture was then concentrated in vacuo and the residue was used directly in the next step without further purification.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customthe residue was used directly in the next step without further purification

Sources & evidence

ORD record
ord-e517312cb484492db5f43249b81d2997
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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