Trifluoroacetic acid → methyl 4-((2S,4S)-4-(2-naphthyloxy)-2-pyrrolidinylmethoxy)benzoate

HRID 1372583Notes

Reaction equation

HRID 1372583 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:19][C@@H:18]([O:20][C:21]2[CH:30]=[CH:29][C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[CH:22]=2)[CH2:17][C@H:16]1[CH2:31][O:32][C:33]1[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=1)=O)(C)(C)C>C(Cl)Cl>[CH:22]1[C:23]2[C:28](=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:29]=[CH:30][C:21]=1[O:20][C@@H:18]1[CH2:19][NH:15][C@H:16]([CH2:31][O:32][C:33]2[CH:42]=[CH:41][C:36]([C:37]([O:39][CH3:40])=[O:38])=[CH:35][CH:34]=2)[CH2:17]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 16093646methyl 4-((2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylmethoxy)benzoate

Product 1

HCID 16093586methyl 4-((2S,4S)-4-(2-naphthyloxy)-2-pyrrolidinylmethoxy)benzoateYield 114.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (6 ml) was added to a solution of methyl 4-((2S,4S)-1-tert-butoxycarbonyl-4-(2-naphthyloxy)-2-pyrrolidinylmethoxy)benzoate (870 mg, 1.74 mmol) in methylene chloride (24 ml). The resulting mixture was stirred overnight at room temperature. To the residue obtained by concentrating the reaction mixture under reduced pressure was added 1N NaOH under ice cooling to make the residue alkaline, followed by extraction with methylene chloride. The extract was washed with saturated brine, dried over anhydrous sodium sulfate and distilled under reduced pressure to remove the solvent. The residue was purified by chromatography on a silica gel column (silica gel: 100 g), whereby from hexane/ethyl acetate (2/1) eluate fractions, the title compound (750 mg, 100%) was obtained as a black oil.

Workup

  1. customTo the residue obtained
  2. concentrationby concentrating the reaction mixture under reduced pressure
  3. additionwas added 1N NaOH under ice cooling
  4. extractionfollowed by extraction with methylene chloride
  5. washThe extract was washed with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customThe residue was purified by chromatography on a silica gel column (silica gel: 100 g), whereby from hexane/ethyl acetate (2/1) eluate fractions

Sources & evidence

ORD record
ord-7aa56ac66aad418589a9cceb20539d01
Source dataset
uspto-grants-2007_01
Patent number
US07157487B2

Reaction notes

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