1-(2-Amino-1,3-thiazol-5-yl)cyclobutan-1-ol → 5-Cyclobutyl-1,3-thiazol-2-amine
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]1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
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).