Reaction #169572

Reaction equation

HCl dioxane

tert-butyl (S)-2-(4-chlorophenyl)-3-(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropylcarbamate

→

(S)-3-amino-2-(4-chlorophenyl)-1-(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one dihydrochloride

Yield 157.4%

Solvents

dioxane

Conditions

Workup

1. 1
   Concentrationafter which it was concentrated
2. 2
   Otherdried on high vacuum line
3. 3
   workup.DISSOLUTIONThe resulting residue was dissolved in minimal MeOH
4. 4
   Otherthe product was triturated by the addition of ether
5. 5
   OtherThe resulting solids were isolated by filtration through Varian quantitative membrane
6. 6
   Filtrationfilter paper with nitrogen pressure
7. 7
   Washrinsed with ether
8. 8
   Otherdried with nitrogen pressure
9. 9
   Otherfurther dried in vacuo

Procedure

4M HCl/dioxane (0.860 ml, 3.44 mmol) was added to a solution of tert-butyl (S)-2-(4-chlorophenyl)-3-(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-3-oxopropylcarbamate (0.043 g, 0.0860 mmol) in dioxane (1.2 mL). The reaction mixture was stirred at room temperature overnight (16 hours), after which it was concentrated and dried on high vacuum line. The resulting residue was dissolved in minimal MeOH, and the product was triturated by the addition of ether. The resulting solids were isolated by filtration through Varian quantitative membrane filter paper with nitrogen pressure, rinsed with ether, dried with nitrogen pressure, and further dried in vacuo to give (S)-3-amino-2-(4-chlorophenyl)-1-(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one dihydrochloride (0.032 g, 78.7% yield) as a white powder. LC/MS (APCI+) m/z 400 [M+H]+.

Source