Trifluoroacetic acid → dimethyl (S)-4-(2-pyrrolidinylmethoxy)isophthalate

HRID 354302Notes

Reaction equation

HRID 354302 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[C:25]([O:27][CH3:28])=[O:26])=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:13][O:14][C:15]1[CH:24]=[CH:23][C:18]([C:19]([O:21][CH3:22])=[O:20])=[CH:17][C:16]=1[C:25]([O:27][CH3:28])=[O:26]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86595076dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]isophthalate

Product 1

HCID 86595072dimethyl (S)-4-(2-pyrrolidinylmethoxy)isophthalateYield 53.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of dimethyl (S)-4-[1-(tert-butoxycarbonyl)-2-pyrrolidinylmethoxy]isophthalate (2.01 g, 5.11 mmol), TFA (20 mL), and CH2Cl2 (25 mL) was stirred for 1.5 hr at room temp. The resulting mixture was concentrated in vacuo and made basic with sat. NaHCO3. The mixture was extracted with CH2Cl2, washed with brine, dried over Na2CO3, and evaporated. The residue was purified by column chromatography on silica-gel with CHCl3—MeOH (9:1, v/v) as eluent to give 0.80 g (53%) dimethyl (S)4-(2-pyrrolidinylmethoxy)isophthalate as a yellow oil. 1H-NMR (CDCl3) δ1.71 (m, 1 H), 1.89 (m, 2 H), 2.00 (m, 1 H), 3.05-3.13 (m, 2 H), 3.67 (m, 1 H), 3.90 (s, 3 H), 3.91 (s, 3 H), 4.05-4.18 (m, 2H), 7.00 (d, 1 H, J=8.8 Hz), 8.14 (dd, 1 H, J=2.4, 8.8 Hz), 8.50 (d, 1 H, J=2.4 Hz).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. extractionThe mixture was extracted with CH2Cl2
  3. washwashed with brine
  4. dry with materialdried over Na2CO3
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica-gel with CHCl3—MeOH (9:1

Sources & evidence

ORD record
ord-b92632aa88fa4a8593452c90b5d6b614
Source dataset
uspto-grants-2004_06
Patent number
US06756378B2

Reaction notes

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