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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 884037Generated: October 31, 2026

1-Methylpiperazine → (2S,4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]-2-[(4-methylpiperazin-1-yl)carbonyl]pyrrolidine

https://huagongshe.com/reaction/884037

Reaction equation

Participants

RoleNameHCIDCharge
Reactant1-MethylpiperazineHCID 53167—
ReactantDiisopropylethylamineHCID 81531—
ReactantMethanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 2733084—
Reactant(4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]-L-prolineHCID 67357391—
SolventDimethylformamideHCID 6228—
Product(2S,4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]-2-[(4-methylpiperazin-1-yl)carbonyl]pyrrolidineHCID 6735916695%

Reaction Steps

(4S)-1-BOC-4-[acetyl(4,4-dimethylcyclohexyl)amino]-L-proline (0.92 g, 2.41 mmol) obtained in Step C was dissolved in DMF (10 mL) and DIPEA (1.05 mL, 6.01 mmol) was added thereto. 1-methylpiperazine (0.32 mL, 2.89 mmol) and HBTU (0.91 g, 2.41 mmol) were also added thereto in order. After the reaction solution was stirred at room temperature for 2 hours, the solution was concentrated in vacuo. The residue was diluted with EtOAc and washed with saturated NaHCO3 aqueous solution. The extracted organic solution was dried over MgSO4, concentrated in vacuo and purified by column chromatography (eluent:MC/MeOH=10/1) to give the title compound (1.06 g, 95%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08236955B2
Source datasetuspto-grants-2012_08
ORD IDord-9a69c0e305f84348ae7e52d0e992989b
Source noteuspto-grants-2012_08