Trifluoroacetic acid → 3-(3,4-Difluorophenyl)-3-methoxypyrrolidine

HRID 575987Notes

Reaction equation

HRID 575987 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C:10]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[C:17]([F:22])[CH:16]=2)([O:13][CH3:14])[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[F: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]=[CH:19][C:18]=1[F:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67402962Tert-butyl 3-(3,4-difluorophenyl)-3-methoxypyrrolidin-1-carboxylate

Product 1

HCID 462192213-(3,4-Difluorophenyl)-3-methoxypyrrolidineYield 63.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation according to Preparation 15. Tert-butyl-3-(3,4-difluorophenyl)-3-methoxypyrrolidin-1-carboxylate (2.65 g, 8.46 mmol), methylene chloride (20 mL) and trifluoroacetic acid (5 mL). Purification on a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1) gave the title compound (1.15 g, 63%). MS m/z (rel. intensity, 70 eV) 198 (46), 183 (79), 171 (bp), 141 (53), 113 (41).

Workup

  1. customPreparation
  2. customaccording to Preparation 15
  3. customPurification
  4. washon a Biotage Isolute SCX-3 SPE column (washed with methanol and eluted with methanol/triethylamine, 4:1)

Sources & evidence

ORD record
ord-62190cfe7d3b41e8b4f67f237fa17eaf
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

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