Trifluoroacetic acid → HCID 70983305, compound

HRID 339016Notes

Reaction equation

HRID 339016 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[CH2:14])[C:10]([O:12][CH3:13])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[CH2:17][N:18]([CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)[CH2:19][Si](C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH2:24]([N:18]1[CH2:17][CH2:14][C:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:4])[CH3:3])=[O:7])([C:10]([O:12][CH3:13])=[O:11])[CH2:19]1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 353442Benzyl(methoxymethyl)((trimethylsilyl)methyl)amineHCID 10932500Methyl 2-((tert-butoxycarbonyl)amino)prop-2-enoate

Product 1

HCID 70983305HCID 70983305, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of methyl 2-(tert-butoxycarbonylamino)acrylate (16.5 g, 82.0 mmol) and N-(Methoxymethyl)-N-(trimethylsilylmethyl)benzylamine (19.5 g, 82.0 mmol) in DCM (400 mL) was added dropwise TFA (0.32 mL) at 0° C. under nitrogen. The reaction mixture was allowed to warm to ambient temperature and stirred overnight. The reaction mixture was diluted with DCM, washed with saturated aqueous NaHCO3 and brine, dried and concentrated under reduced pressure. The residue was purified by flash chromatography on silica gel (3% MeOH in DCM) to give methyl 1-benzyl-3-(tert-butoxycarbonylamino)pyrrolidine-3-carboxylate (21.7 g, 79%).

Workup

  1. washwashed with saturated aqueous NaHCO3 and brine
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash chromatography on silica gel (3% MeOH in DCM)

Sources & evidence

ORD record
ord-9113e490df6b424199b55cfbfb3e82ad
Source dataset
uspto-grants-2014_11
Patent number
US08889704B2

Reaction notes

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