Trifluoroacetic acid → Methyl 4-(4,4-difluoro-2-pyrrolidinylmethoxy)benzoate

HRID 350499Notes

Reaction equation

HRID 350499 reaction equation
C(OC([N:8]1[CH2:12][C:11]([F:14])([F:13])[CH2:10][CH: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([O-])(O)=O.[Na+]>C(Cl)Cl>[F:14][C:11]1([F:13])[CH2:12][NH:8][CH: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

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 69332927Methyl 4-[1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethoxy]benzoate

Product 1

HCID 23512388Methyl 4-(4,4-difluoro-2-pyrrolidinylmethoxy)benzoateYield 91%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 4-[1-(tert-butoxycarbonyl)-4,4-difluoro-2-pyrrolidinylmethoxy]benzoate (830 mg, 2.23 mmol) and TFA (5 ml) in CH2Cl2 (5 ml) was stirred for 3 h and concntrated in vacuo. The residue was made basic with sat. NaHCO3 and extracted with CHCl3 (2×200 ml). The combined extracts were dried over K2CO3 and concntrated in vacuo to give methyl 4-(4,4-difluoro-2-pyrrolidinylmethoxy)benzoate (550 mg, 91%) as a pale yellow solid. 1H-NMR (CDCl3) δ 2.19 (m, 1 H), 2.43 (m, 1 H), 3.19–3.41 (m, 2 H), 3.77 (m, 1 H), 3.89 (s, 3 H), 4.00–4.09 (m, 2 H), 6.92 (d, J=9.0 Hz, 2 H), 7.99 (d, J=9.0 Hz, 2 H); MS (FAB) m/z 272 (M++1); Anal. Calcd for C13H15F2NO3: C, 57.56; H, 5.57; N, 5.16. Found: C, 57.65; H, 5.67; N, 5.16.

Workup

  1. extractionextracted with CHCl3 (2×200 ml)
  2. dry with materialThe combined extracts were dried over K2CO3

Sources & evidence

ORD record
ord-db50f7eee8be4f02afb8cb398dff8dd3
Source dataset
uspto-grants-2007_02
Patent number
US07179819B2

Reaction notes

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