Trifluoroacetic acid → 3-(3-Chloro-4-fluorophenyl)-3-methoxypyrrolidine

HRID 575985Notes

Reaction equation

HRID 575985 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]([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]=[CH:19][C:18]=1[F:21]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67402089Tert-butyl 3-(3-chloro-4-fluorophenyl)-3-methoxypyrrolidin-1-carboxylate

Product 1

HCID 462193563-(3-Chloro-4-fluorophenyl)-3-methoxypyrrolidineYield 88%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Preparation according to Preparation 15. Tert-butyl-3-(3-chloro-4-fluorophenyl)-3-methoxypyrrolidin-1-carboxylate (1.81 g, 5.5 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 (1.11 g, 88%). MS m/z (rel. intensity, 70 eV) 214 (38), 199 (73), 187 (bp), 157 (40), 133 (39).

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-a14c0dcf629943dd8c58c01596667069
Source dataset
uspto-grants-2015_05
Patent number
US09035073B2

Reaction notes

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