Hydrochloric Acid → (S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-((S)-pyrrolidin-2-yl)ethanone

HRID 1916396Notes

Reaction equation

HRID 1916396 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C@@H:28]2[CH2:32][CH2:31][CH2:30][N:29]2C(OC(C)(C)C)=O)[C:9]([N:11]2[CH2:16][CH2:15][N:14]([C:17]3[C:18]4[C@H:25]([CH3:26])[CH2:24][C@@H:23]([OH:27])[C:19]=4[N:20]=[CH:21][N:22]=3)[CH2:13][CH2:12]2)=[O:10])=[CH:4][CH:3]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C@@H:28]2[CH2:32][CH2:31][CH2:30][NH:29]2)[C:9]([N:11]2[CH2:12][CH2:13][N:14]([C:17]3[C:18]4[C@H:25]([CH3:26])[CH2:24][C@@H:23]([OH:27])[C:19]=4[N:20]=[CH:21][N:22]=3)[CH2:15][CH2:16]2)=[O:10])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 66845588HCID 66845588, compound

Product 1

HCID 25170562(S)-2-(4-chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-((S)-pyrrolidin-2-yl)ethanone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

(S)-tert-butyl 2-((S)-1-(4-chlorophenyl)-2-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-oxoethyl)pyrrolidine-1-carboxylate (0.74 g, 1.331 mmol) was dissolved in dioxane (3 mL) and treated with 4M hydrogen chloride in dioxane (8.317 mL, 33.27 mmol). The mixture was stirred at ambient temperature for 8 hours. The reaction was concentrated in vacuo, re-dissolved and re-concentrated from MeOH three times. Then the residue was re-dissolved in MeOH (3 mL) and added dropwise to stirred Et2O (100 mL). After stirring for 30 minutes, the solid was collected, washed with Et2O, and then air-dried under a blanket of nitrogen. (S)-2-(4-Chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-((S)-pyrrolidin-2-yl)ethanone was recovered as a white solid, (0.47 g, 79%). MS (ESI+) [M+H] 456.1/458.1

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionre-dissolved
  3. concentrationre-concentrated from MeOH three times
  4. dissolutionThen the residue was re-dissolved in MeOH (3 mL)
  5. additionadded dropwise
  6. stirringto stirred Et2O (100 mL)
  7. stirringAfter stirring for 30 minutes
  8. customthe solid was collected
  9. washwashed with Et2O
  10. customair-dried under a blanket of nitrogen
  11. custom(S)-2-(4-Chlorophenyl)-1-(4-((5R,7R)-7-hydroxy-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)piperazin-1-yl)-2-((S)-pyrrolidin-2-yl)ethanone was recovered as a white solid, (0.47 g, 79%)

Sources & evidence

ORD record
ord-e3375455e5f24627a49d1d2ab144aa6e
Source dataset
uspto-grants-2013_12
Patent number
US08618097B2

Reaction notes

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