Reaction #74409

Reaction equation

tert-butyl 4-((2-((2S)-bicyclo[2.2.1]heptan-2-ylamino)-5-methyl-4-oxo-4,5-dihydrothiazol-5-yl)methyl)piperidine-1-carboxylate

HCl

→

title compound

Yield 99.7%

2-((2S)-Bicyclo[2.2.1]heptan-2-ylamino)-5-methyl-5-(piperidin-4-ylmethyl)thiazol-4(5H)-one

Yield 99.7%

Solvents

EtOAc

Conditions

Workup

1. 1
   Concentrationthe reaction mixture was concentrated in vacuo
2. 2
   workup.ADDITIONAqueous Na2CO3 (2.0 M, 20 mL) was then added
3. 3
   Otherwater was removed in vacuo
4. 4
   OtherThe residue was then triturated with 10% MeOH—CH2Cl2 (6×100 mL)
5. 5
   Otherthe combined triturating solution
6. 6
   Concentrationwere concentrated in vacuo
7. 7
   workup.DISSOLUTIONThe crude product was dissolved in CH2Cl2
8. 8
   Filtrationfiltered
9. 9
   Concentrationconcentrated in vacuo

Procedure

A mixture of tert-butyl 4-((2-((2S)-bicyclo[2.2.1]heptan-2-ylamino)-5-methyl-4-oxo-4,5-dihydrothiazol-5-yl)methyl)piperidine-1-carboxylate (1.42 g, 3.37 mmol, 1.0 eq) in 50 mL of a 4.7 M HCl solution in EtOAc was stirred at roomtemperature. After 4 h, the reaction mixture was concentrated in vacuo. Aqueous Na2CO3 (2.0 M, 20 mL) was then added, and water was removed in vacuo. The residue was then triturated with 10% MeOH—CH2Cl2 (6×100 mL), and the combined triturating solution were concentrated in vacuo. The crude product was dissolved in CH2Cl2, filtered, and concentrated in vacuo to afford the title compound as a light orange solid (1.08 g). MS (ESI, pos. ion) m/z: 322 (M+H).

Source