1-(2-Amino-1,3-thiazol-5-yl)cyclobutan-1-ol → 5-Cyclobutyl-1,3-thiazol-2-amine

HRID 1446688Notes

Reaction equation

HRID 1446688 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:7]2(O)[CH2:10][CH2:9][CH2:8]2)=[CH:5][N:6]=1>FC(F)(F)C(O)=O.[OH-].[OH-].[Pd+2]>[CH:7]1([C:4]2[S:3][C:2]([NH2:1])=[N:6][CH:5]=2)[CH2:10][CH2:9][CH2:8]1

Participants

4

Reactant 1

HCID 227313761-(2-Amino-1,3-thiazol-5-yl)cyclobutan-1-ol

Product 1

HCID 129914235-Cyclobutyl-1,3-thiazol-2-amineYield 60%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 6422Trifluoroacetic acidSolvent

Procedure

Hydrogenate 1-(2-amino-thiazol-5-yl)-cyclobutanol (0.94 g, 5.52 mmol, 1.0 eq.) in trifluoroacetic acid (16 mL) in the presence of Pearlman's catalyst (0.16 g) under H2 (52 psi) for over night. Filter off the catalyst. Wash with methanol. Concentrate in vacuo. Add dichloromethane (100 mL) to the residue. Wash the organic layer with sodium bicarbonate (sat. 2×30 mL), aqueous saturated sodium chloride (2×20 mL) and water (2×30 mL). Dry the organic phase over MgSO4 and filter the drying reagent off. Concentrate in vacuo. Purify by column chromatography (0%→5% methanol in dichloromethane) to afford product (0.508 g, 60%). MS(ES), m/z 155 (M+1).

Workup

  1. filtrationFilter off the catalyst
  2. washWash with methanol
  3. concentrationConcentrate in vacuo
  4. washWash the organic layer with sodium bicarbonate (sat. 2×30 mL), aqueous saturated sodium chloride (2×20 mL) and water (2×30 mL)
  5. dry with materialDry the organic phase over MgSO4
  6. filtrationfilter the drying reagent off
  7. concentrationConcentrate in vacuo
  8. customPurify by column chromatography (0%→5% methanol in dichloromethane)

Sources & evidence

ORD record
ord-62c4544ce3a340eeb3f6dd3673390358
Source dataset
uspto-grants-2010_02
Patent number
US07666879B2

Reaction notes

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