Trifluoroacetic acid → 1-Benzyl-3-(trifluoromethyl)pyrrolidine-3-carboxylic acid

HRID 1888

Reaction equation

HRID 1888 reaction equation
[F:1][C:2]([F:9])([F:8])[C:3](=[CH2:7])[C:4]([OH:6])=[O:5].[CH2:10]([N:17]([CH2:21][Si](C)(C)C)[CH2:18]OC)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:10]([N:17]1[CH2:18][CH2:7][C:3]([C:2]([F:9])([F:8])[F:1])([C:4]([OH:6])=[O:5])[CH2:21]1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 5876942-(Trifluoromethyl)acrylic acid

Product 1

HCID 196913671-Benzyl-3-(trifluoromethyl)pyrrolidine-3-carboxylic acidYield 58.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

2-(Trifluoromethyl)acrylic acid (2.48 g, 20 mmol) was dissolved in 30 mL of dry methylene chloride, a solution of 4.75 g (20 mmol) of N-benzyl-N-(methoxymethyl)-trimethylsilylmethylamine in 20 mL of dry methylene chloride was added dropwise under N2 at 0° C. To this solution was added 2 mL of TFA, and the solution was stirred for 2 hours at room temperature. The white precipitate was collected, washed and dried to give 3.22 g of the title compound.

Workup

  1. customThe white precipitate was collected
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-593685df77934601a60a768a24ebbaa0
Source dataset
uspto-grants-1998_03
Patent number
US05726182

Linked notes

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