Trifluoroacetic acid → Methyl 3-[1-(acetyloxy)ethyl]-1-(phenylmethyl)-3-pyrrolidinecarboxylate

HRID 1038049Notes

Reaction equation

HRID 1038049 reaction equation
FC(F)(F)C(O)=O.[CH3:8][O:9][C:10](=[O:19])[C:11](=[CH2:18])[CH:12]([O:14][C:15](=[O:17])[CH3:16])[CH3:13].CO[CH2:22][N:23]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:24][Si](C)(C)C>C(Cl)Cl>[CH3:8][O:9][C:10]([C:11]1([CH:12]([O:14][C:15](=[O:17])[CH3:16])[CH3:13])[CH2:18][CH2:22][N:23]([CH2:29][C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH2:24]1)=[O:19]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 5102926Methyl 3-acetoxy-2-methylenebutyrate

Product 1

HCID 57685792Methyl 3-[1-(acetyloxy)ethyl]-1-(phenylmethyl)-3-pyrrolidinecarboxylateYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (0.5 g, 4.38 mmol) was added to a solution of methyl-3-acetoxy-2-methylenebutyrate (5 g, 29.03 mmol) (1) and N-Methoxymethyl-N-trimethylsilylmethylbenzylamine (6.89 g, 29.03 mmol) (2) in MeCl2 (100 ml) at 0° C., then stirred overnight at room temperature. The solvent was evaporated, and residue extracted with EtOAc (200 ml), NaHCO3 (30 ml and H2O (100 ml). The organic layer was separated, dried (MgSO4), filtered and solvent evaporated yielding an oil which chromatographed on silica gel eluting with 30% v/v (EtOAc/hexanes) yielding product (3) as colorless oil (7.53 g, 85% yield). ESMS MH, 306 (C17H23NO4)

Workup

  1. customThe solvent was evaporated
  2. extractionresidue extracted with EtOAc (200 ml), NaHCO3 (30 ml and H2O (100 ml)
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customsolvent evaporated
  7. customyielding an oil which
  8. customchromatographed on silica gel eluting with 30% v/v (EtOAc/hexanes)

Sources & evidence

ORD record
ord-bae0bf636cc34bc68ff34193e8fb82f2
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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