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

HRID 1038077Notes

Reaction equation

HRID 1038077 reaction equation
F[C:2](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]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[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])[CH2:2][CH2:22][N:23]([CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:18]1)=[O:19]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 5102926Methyl 3-acetoxy-2-methylenebutyrateHCID 23062047Benzyl-methoxymethyl-trimethylsilanyl-amine

Product 1

HCID 57685792Methyl 3-[1-(acetyloxy)ethyl]-1-(phenylmethyl)-3-pyrrolidinecarboxylate

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) and N-methoxymethyl-N-trimethylsilyl benzylamine (6.89 g, 29.03 mmol) in MeCl2 (50 ml) at 0° C. then stirred overnight at room temperature. The solvent was evaporated and the residue extracted with EtOAc (200 ml) and H2O (50 ml) and saturated NaHCO3 solution (50 ml). The organic layer was separated, dried over MgSO4 filtered and evaporated solvent. The residue chromatographed on silica gel eluting with (v:v) EtOAc:hexanes 3:1 yielding compound 2N as a colorless oil (7 g, 81.7%) LCMS (MH, 306) Retention time=2.08 minutes.

Workup

  1. customThe solvent was evaporated
  2. extractionthe residue extracted with EtOAc (200 ml) and H2O (50 ml) and saturated NaHCO3 solution (50 ml)
  3. customThe organic layer was separated
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. customevaporated solvent
  7. customThe residue chromatographed on silica gel eluting with (v:v) EtOAc:hexanes 3:1 yielding compound 2N as a colorless oil (7 g, 81.7%) LCMS (MH, 306) Retention time=2.08 minutes

Sources & evidence

ORD record
ord-e6e5e2a59274450bb38d85ae9bc463d6
Source dataset
uspto-grants-2013_10
Patent number
US08546404B2

Reaction notes

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