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

HRID 1886

Reaction equation

HRID 1886 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.FC(F)(F)C(O)=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 acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A 2.48 g sample of 2-(trifluoromethyl)acrylic acid was dissolved in 40 mL of dry methylene chloride, and a solution of 4.75 g of N-benzyl-N-(methoxymethyl)-trimethylsilylmethylamine in 20 mL of dry methylene chloride was added dropwise under N2 at 0° C. To this mixture was added 2 mL of trifluoroacetic acid, and the mixture was stirred for 2 hours at room temperature. The product was removed by filtration, washed and dried to give the title product.

Workup

  1. customThe product was removed by filtration
  2. washwashed
  3. customdried

Sources & evidence

ORD record
ord-7b48bd4f78a1409eb2c2a20f041bf0c4
Source dataset
uspto-grants-1998_03
Patent number
US05726182

Linked notes

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