Acetic Acid → HCID 117600798, compound

HRID 571374Notes

Reaction equation

HRID 571374 reaction equation
[CH3:1][N:2]1[CH2:6][C@@H:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:16])([F:15])[F:14])[C@H:4]([N+:17]([O-])=O)[CH2:3]1.C(O)(=O)C>CO.[Zn]>[CH3:1][N:2]1[CH2:6][C@@H:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=2[C:13]([F:14])([F:15])[F:16])[C@H:4]([NH2:17])[CH2:3]1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 117601661HCID 117601661, compound

Product 1

HCID 117600798HCID 117600798, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

Racemic (3R,4S) and (3S,4R)-1-Methyl-3-nitro-4-(2-(trifluoromethyl)phenyl)-pyrrolidine (296.8 mg, 1.082 mmol) was dissolved in MeOH (5 mL) and Acetic Acid (5 mL) then zinc (354 mg, 5.41 mmol) was added at 0° C. The reaction mixture was warmed to room temperature and stirred under nitrogen overnight. The suspension was filtered over celite and washed with methanol. The filtrate was concentrated in vacuo and the residue was suspended in ethyl acetate, cooled in an ice bath, and basified with conc. NH4OH. The organic phase was separated and washed with brine. The organic layers were combined and dried over sodium sulfate, filtered, and concentrated in vacuo to give racemic (3R,4S) and (3S,4R)-1-methyl-4-(2-(trifluoromethyl)phenyl)pyrrolidin-3-amine (230.9 mg, 0.945 mmol, 87%), which was carried onto the next step without further purification. MS ESI calc'd. For C12H15F3N2 [M+1]+ 245, found 245.

Workup

  1. filtrationThe suspension was filtered over celite
  2. washwashed with methanol
  3. concentrationThe filtrate was concentrated in vacuo
  4. temperaturecooled in an ice bath
  5. customThe organic phase was separated
  6. washwashed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-63197d673dd9431389dc4705aab61858
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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