Reaction #169551

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-oxopropyl(isopropyl)carbamate

→

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

Yield 189.5%

Solvents

dioxane

Conditions

Workup

1. 1
   ConcentrationThe reaction mixture was concentrated to dryness
2. 2
   Otherdried on a high vacuum line
3. 3
   workup.DISSOLUTIONThe resulting residue was dissolved in minimal MeOH
4. 4
   workup.ADDITIONthe solution was added dropwise to a stirring solution of ether, which
5. 5
   Otherto form
6. 6
   OtherThe resulting precipitate was isolated by filtration through a medium frit funnel with nitrogen pressure
7. 7
   Washrinsed with ether
8. 8
   Otherdried with nitrogen pressure
9. 9
   Otherdried in vacuo

Procedure

4M HCl/dioxane (7.83 ml, 31.3 mmol) was added to a slightly cloudy 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-oxopropyl(isopropyl)carbamate (0.679 g, 1.25 mmol) in dioxane (8 mL). The reaction mixture was stirred overnight under nitrogen (16 hours). The reaction mixture was concentrated to dryness and dried on a high vacuum line. The resulting residue was dissolved in minimal MeOH, and the solution was added dropwise to a stirring solution of ether, which caused a white precipitate to form. The resulting precipitate was isolated by filtration through a medium frit funnel with nitrogen pressure, rinsed with ether, dried with nitrogen pressure, dried in vacuo and then further in a 55° C. high vacuum oven for 2 days to give (S)-2-(4-chlorophenyl)-3-(isopropylamino)-1-(4-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)propan-1-one dihydrochloride (0.610 g, 94.6% yield) as a white powder.

Source