Reaction #1256771

Reaction equation

NaHCO3

3-piperazin-1-yl-isoxazolo[4,5-c]pyridine dihydrochloride

trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester

intermediate H

trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester

Et3N

→

title compound

Yield 72.2%

{Trans-4-[2-(4-Isoxazolo[4,5-c]pyridin-3-yl-piperazin-1-yl)-ethyl]-cyclohexyl}-carbamic acid tert-butyl ester

Yield 72.2%

Solvents

CH2Cl2

Conditions

Workup

1. 1
   Extractionthe product was extracted with 2 portions of CH2Cl2
2. 2
   OtherAfter drying
3. 3
   Other(MgSO4) and evaporation of the solvent the product
4. 4
   Otherwas purified by flash chromatography (50 g SiO2, EtOAc/MeOH 100:0→80:20)

Procedure

A solution in CH2Cl2 (10 ml) of 3-piperazin-1-yl-isoxazolo[4,5-c]pyridine dihydrochloride (840 mg, 3.0 mmol) and trans-[4-(2-oxo-ethyl)-cyclohexyl]-carbamic acid tert-butyl ester (904 mg, 3.7 mmol; intermediate H; prepared according to WO2007/093540) was treated with Et3N (629 mg, 6.2 mmol) before addition of Na(AcO)3BH (1.03 g, 5 mmol). The reaction mixture was stirred 16 h at r.t., then sat. aq. NaHCO3 was added and the product was extracted with 2 portions of CH2Cl2. After drying (MgSO4) and evaporation of the solvent the product was purified by flash chromatography (50 g SiO2, EtOAc/MeOH 100:0→80:20) to obtain 930 mg (71%) of the title compound as an off white solid. m/z=430.3 ([M+H]+).

Source