Trifluoroacetic acid → HCID 54443836, compound

HRID 338974Notes

Reaction equation

HRID 338974 reaction equation
[F:1][CH2:2][C:3](=[CH2:9])[C:4]([O:6][CH2:7][CH3:8])=[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>ClCCl>[CH2:10]([N:17]1[CH2:18][CH2:9][C:3]([CH2:2][F:1])([C:4]([O:6][CH2:7][CH3:8])=[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 12815505Ethyl 2-(fluoromethyl)prop-2-enoate

Product 1

HCID 54443836HCID 54443836, compoundYield 58.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
1 °C

Procedure

To a solution of ethyl 2-(fluoromethyl)acrylate (2.54 g, 19.2 mmol) and N-benzyl-N-(methoxymethyl)trimethylsilylmethylamine (5.1 mL, 19.2 mmol) in dichloromethane (15 mL) cooled to 0° C. in an ice bath, was added 1M solution of TFA in dichloromathane (1.8 mL), and the resulting mixture stirred at 0-2° C. for 75 minutes. The reaction was diluted with dichloromethane (20 mL) and washed with saturated sodium bicarbonate solution, brine and dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by column chromatography (Biotage 40M; 10% ethyl acetate/hexanes) to afford ethyl 1-benzyl-3-(fluoromethyl)pyrrolidine-3-carboxylate (2.98 g, 58%).

Workup

  1. washwashed with saturated sodium bicarbonate solution, brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography (Biotage 40M; 10% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-2a96dd5f085247f09ba6867fcb7393e3
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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