Methanol → 3-Isopropylpyrrolidine trifluoroacetate

HRID 969202Notes

Reaction equation

HRID 969202 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[C:8]([C:11]1[CH2:12][NH:13][CH2:14][CH:15]=1)([CH3:10])=[CH2:9].CO>[Pd]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:8]([CH:11]1[CH2:15][CH2:14][NH:13][CH2:12]1)([CH3:10])[CH3:9]

Participants

4

Reactant 2

HCID 887MethanolHCID 666625073-isopropenyl-2,5-dihydro-1H-pyrrole trifluoroacetate

Product 1

HCID 666617803-Isopropylpyrrolidine trifluoroacetate

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

To a solution of 3-isopropenyl-2,5-dihydro-1H-pyrrole trifluoroacetate (2.09 g, 0.00936 mol) in methanol (100.0 mL, 2.469 mol) was added 1.3 g of Pd (10% wt. on activated carbon), then the mixture was hydrogenated on par shaker at 43 psi for 3 h. The mixture was filtered and the filtrate was concentrated in vacuo. The residue was dried under high vacuum to afford the product as a white solid. LC-MS (M+H) 114.2 (base) [M+H) 130.1 base, for the corresponding alcohol].

Workup

  1. filtrationThe mixture was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was dried under high vacuum

Sources & evidence

ORD record
ord-b3d94b989a9f4f50bc32c96396b70c9d
Source dataset
uspto-grants-2007_12
Patent number
US07304081B2

Reaction notes

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