Trifluoroacetic acid → HCID 54443836, compound

HRID 1016077Notes

Reaction equation

HRID 1016077 reaction equation
[CH2:1]([N:8]([CH2:12][Si](C)(C)C)[CH2:9]OC)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:17][CH2:18][C:19](=[CH2:25])[C:20]([O:22][CH2:23][CH3:24])=[O:21].C(O)(C(F)(F)F)=O.C([O-])(O)=O.[Na+]>C(Cl)Cl.CCOC(C)=O.CCCCCC.C(OCC)(=O)C>[CH2:1]([N:8]1[CH2:9][CH2:25][C:19]([CH2:18][F:17])([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:12]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 4

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 516892Sodium BicarbonateHCID 12815505Ethyl 2-(fluoromethyl)prop-2-enoate

Product 1

HCID 54443836HCID 54443836, compoundYield 23%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolventHCID 21226206Ethyl acetate hexaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-benzyl-1-methoxy-N-[(trimethylsilyl)methyl]methanamine (2.5 g, 21 mmol) and ethyl 2-(fluoromethyl)acrylate (5.0 g, 21 mmol) in methylene chloride (30 mL) was added TFA (0.15 ml, 2.1 mmol) at 0° C. The reaction mixture was stirred at 0° C. overnight. 20 mL of saturated NaHCO3 aqueous solution and 20 mL of ethyl acetate were added to quench the reaction. The organic layer was separated, and the aqueous layer was extracted twice with EtOAc (20 mL×2). The combined organic extracts were dried over MgSO4 and evaporated to give an oil residue. Chromatography on silica gel with 10% EtOAc-Hexane afforded 1.27 g (4.8 mmol, yield: 23%) of ethyl 1-benzyl-3-(fluoromethyl)pyrrolidine-3-carboxylate: 1H NMR (400 MHz, CDCl3) δ 7.39-7.20 (5H, m), 4.62-4.44 (2H, m), 4.18-4.21 (2H, m), 3.62 (2H, s), 2.81-2.72 (2H, m), 2.60-2.50 (2H, m), 2.22 (2H, s), 1.25 (3H, t, J=6.7 Hz); MS (m/e): 266 (M+1)+.

Workup

  1. customto quench
  2. customthe reaction
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted twice with EtOAc (20 mL×2)
  5. dry with materialThe combined organic extracts were dried over MgSO4
  6. customevaporated
  7. customto give an oil residue

Sources & evidence

ORD record
ord-94609dad4ec94daebd29400504e63bbf
Source dataset
uspto-grants-2011_07
Patent number
US07985730B2

Reaction notes

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