Trifluoroacetic acid → HCID 69333312, compound

HRID 354447Notes

Reaction equation

HRID 354447 reaction equation
C([N:8]1[C@H:12]([CH3:13])[CH2:11][CH2:10][C@H:9]1[CH2:14][O:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)(OC(C)(C)C)=O.FC(F)(F)C(O)=O>C(Cl)Cl>[CH3:13][C@H:12]1[NH:8][C@H:9]([CH2:14][O:15][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)[CH2:10][CH2:11]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20737849HCID 20737849, compound

Product 1

HCID 69333312HCID 69333312, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 4-[N-Boc-5-(R)-methyl-2-(S)-pyrrolidinylmethoxy]benzoate (1.29 g, 3.70 mmol) in CH2Cl2 (30 ml) was added trifluoroacetic acid (10 ml) at rt, and the resulting mixture was stirred for 35 min. The mixture was concentrated in vacuo and poured into aq.NaHCO3, then extracted with CHCl3. The organic layer was washed with water, drying over anhydrous Na2SO4, and concentrated in vacuo to give methyl 4-[5-(R)-methyl-2-(S)-pirrolidinyl methoxy]benzoate (871 mg, 95%) as a colorless oil. The product was used for next reactions without further purification. 1H-NMR (CDCl3) δ1.18 (d, J=6.4 Hz, 3 H), 1.30-1.40 (m, 1 H), 1.59-1.67 (m, 1 H), 1.87-1.97 (m, 2 H), 3.19-3.27 (m, 1 H), 3.49-3.55 (m, 1 H), 3.87 (s, 3 H), 3.89-4.05 (m, 2 H), 6.89 (d, J=8.8 Hz, 2 H), 7.96 (d, J=8.8 Hz, 2 H); MS (ESI) m/z, 250 (M++H)

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. additionpoured into aq
  3. extractionNaHCO3, then extracted with CHCl3
  4. washThe organic layer was washed with water
  5. dry with materialdrying over anhydrous Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c3160fa3ec664b1693f0df258b456fd3
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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