Trifluoroacetic acid → HCID 16093585, compound

HRID 354429Notes

Reaction equation

HRID 354429 reaction equation
C(OC([N:8]1[CH2:12][C@@H:11]([O:13][CH3:14])[CH2:10][C@H:9]1[CH2:15][O:16][C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:14][O:13][C@@H:11]1[CH2:12][NH:8][C@H:9]([CH2:15][O:16][C:17]2[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=2)[CH2:10]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 16093620HCID 16093620, compound

Product 1

HCID 16093585HCID 16093585, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of methyl 4-[(2S,4S)-1tert-butoxycarbonyl-4-methoxy-2-pyrrolidinyl]methoxybenzoate (2.38 g, 3.61 mmol) in CH2Cl2 (46 ml) was added TFA (23 ml) at room temperature. After 14 h stirring, the mixture was concentrated in vacuo. The residue was diluted by the addition of CH2Cl2 and 1 N NaOH, and extracted with CH2Cl2. The combined extracts were washed with brine, dried over Na2SO4, which was concentrated in vacuo. The residue was chromatographed on silica gel [50 g, CHCl3/MeOH (20/1)], to give methyl 4-[(2S,4S)-4-methoxy-2-pyrrolidinyl]methoxybenzoate (950 mg, 99%) as a yellow oil. 1H-NMR (CDCl3) δ2.16 (t, J=5.3 Hz, 1H), 2.72 (s, 1H), 2.95 (d, J=6.8 Hz, 1H), 3.11 (d, J=11.0 Hz, 1H), 3.26 (t, J=1.9 Hz, 3H), 3.52 (br, 1H), 3.84 (d, J=1.7 Hz, 3H), 3.92 (s, 1H), 4.00 (d, J=4.1 Hz, 2H), 6.88 (m, 2H), 7.94 (m, 2H).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionThe residue was diluted by the addition of CH2Cl2 and 1 N NaOH
  3. extractionextracted with CH2Cl2
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4, which
  6. concentrationwas concentrated in vacuo
  7. customThe residue was chromatographed on silica gel [50 g, CHCl3/MeOH (20/1)]

Sources & evidence

ORD record
ord-730e15909c364fcfa8d17a5194815055
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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