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

HRID 1188156Notes

Reaction equation

HRID 1188156 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>ClCCl>[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 dichloromethane (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%). The amine was converted to the oxalic acid salt and recrystallized from methanol/diethyl ether: M.p. 169-170° C. 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-34a237ee6b464a5da8f2d214064c8c0e
Source dataset
uspto-grants-2014_03
Patent number
US08673962B2

Reaction notes

Loading…