Hydrochloric Acid → 2,2-Dimethyl-1-(5-methyl-1,3,4-oxadiazol-2-yl)propan-1-amine

HRID 1480246Notes

Reaction equation

HRID 1480246 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[CH:3]([NH:10]S(C(C)(C)C)=O)[C:4]1[O:5][C:6]([CH3:9])=[N:7][N:8]=1.Cl.O1CCOCC1>CO>[CH3:1][C:2]([CH3:18])([CH3:17])[CH:3]([C:4]1[O:5][C:6]([CH3:9])=[N:7][N:8]=1)[NH2:10]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 90204274HCID 90204274, compound

Product 1

HCID 689184512,2-Dimethyl-1-(5-methyl-1,3,4-oxadiazol-2-yl)propan-1-amineYield 58%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of N-[2,2-dimethyl-1-(5-methyl-1,3,4-oxadiazol-2-yl)propyl]-2-methyl-propane-2-sulfinamide (example 174a, 462 mg, 1.69 mmol) in methanol (10 ml) was added a 4M solution of hydrochloric acid in dioxane (845 μl, 3.38 mmol). The reaction was stirred for 1 hour at room temperature. The reaction was then concentrated in vacuo and the residue was dissolved in ethylacetate. The organic phase was extracted with a 2M aqueous solution of sodium carbonate. The organic phase was collected and the aqueous phase was back-extracted with ethylacetate. Combined organic phases were dried over sodium sulfate and evaporated down to dryness. The crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient to yield the title compound (165 mg, 58%). MS (ESI, m/z): 170.5 (M+H+).

Workup

  1. concentrationThe reaction was then concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethylacetate
  3. extractionThe organic phase was extracted with a 2M aqueous solution of sodium carbonate
  4. customThe organic phase was collected
  5. extractionthe aqueous phase was back-extracted with ethylacetate
  6. dry with materialCombined organic phases were dried over sodium sulfate
  7. customevaporated down to dryness
  8. customThe crude material was purified by flash chromatography on silica eluting with a dichloromethane/methanol gradient

Sources & evidence

ORD record
ord-d8a956f662be48a4988c4d77e02f221f
Source dataset
uspto-grants-2016_08
Patent number
US09409866B2

Reaction notes

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