Acetic Acid → HCID 89525909, compound

HRID 571382Notes

Reaction equation

HRID 571382 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[CH3:13])[C@H:4]([N+:14]([O-])=O)[C@@H:3]1[CH3:17].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[CH3:13])[C@H:4]([NH2:14])[C@@H:3]1[CH3:17]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 89525816HCID 89525816, compound

Product 1

HCID 89525909HCID 89525909, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

(2R,3R,4S)+(2S,3S,4R)-1,2-dimethyl-3-nitro-4-(o-tolyl) pyrrolidine (28 mg, 0.12 mmol) was dissolved in 1 ml MeOH and Acetic Acid (2.0 ml) and charged with ZINC (39.1 mg, 0.598 mmol). The reaction was allowed to stir overnight at rt. The solution was filtered through celite and concentrated in vacuo. The residue was dissolved in 2 mL MeOH and desalted on ps-bicarb. The solvents were removed in vacuo to afford (2R,3R,4S)+(2S,3S,4R)-1,2-dimethyl-4-(o-tolyl)pyrrolidin-3-amine (17 mg, 0.08 mmol, 70% yield). LC/MS M+H 205.2

Workup

  1. filtrationThe solution was filtered through celite and
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in 2 mL MeOH
  4. customThe solvents were removed in vacuo

Sources & evidence

ORD record
ord-ab51c3a78bd746ec876af2b8b03a748b
Source dataset
uspto-grants-2015_05
Patent number
US09023865B2

Reaction notes

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