Trifluoroacetic acid → 3-(3-Chloro-5-fluorophenyl)-3-methoxypyrrolidine

HRID 575984Notes

Reaction equation

HRID 575984 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[C:19]([F:21])[CH:18]=[C:17]([Cl:22])[CH:16]=2)([O:13][CH3:14])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[Cl:22][C:17]1[CH:16]=[C:15]([C:10]2([O:13][CH3:14])[CH2:11][CH2:12][NH:8][CH2:9]2)[CH:20]=[C:19]([F:21])[CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67402360Tert-butyl 3-(3-chloro-5-fluorophenyl)-3-methoxypyrrolidin-1-carboxylate

Product 1

HCID 462192233-(3-Chloro-5-fluorophenyl)-3-methoxypyrrolidineYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl-3-(3-chloro-5-fluorophenyl)-3-methoxypyrrolidin-1-carboxylate (1.57 g, 4.77 mmol) in methylene chloride (20 mL), was added trifluoroacetic acid (5 mL). The mixture was stirred for 1 h at ambient temperature after which the solvent was evaporated. Purification on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1) gave the title compound (0.845 g, 77%). MS m/z (rel. intensity, 70 eV) 199 (bp), 187 (93), 157 (61), 133 (66), 129 (59).

Workup

  1. customwas evaporated
  2. customPurification
  3. washon a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1)

Sources & evidence

ORD record
ord-5a5b18728b7a4618a0b957e406fcf1ad
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

Loading…