Potassium Carbonate → 1,3-Dimethyl 2-(4-((tert-butoxy)carbonyl)piperazin-1-yl)propanedioate

HRID 517484Notes

Reaction equation

HRID 517484 reaction equation
C(=O)([O-])[O-].[K+].[K+].Br[CH:8]([C:13]([O:15][CH3:16])=[O:14])[C:9]([O:11][CH3:12])=[O:10].[N:17]1([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]1>C(#N)C>[C:26]([O:25][C:23]([N:17]1[CH2:22][CH2:21][N:20]([CH:8]([C:13]([O:15][CH3:16])=[O:14])[C:9]([O:11][CH3:12])=[O:10])[CH2:19][CH2:18]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 70087Dimethyl bromomalonateHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 578486921,3-Dimethyl 2-(4-((tert-butoxy)carbonyl)piperazin-1-yl)propanedioateYield 97%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

19.5 g (141 mmol) of potassium carbonate then 19.5 ml (134 mmol) of dimethyl bromomalonate are added to a solution of 25 g (134 mmol) of tert-butyl piperazine-1-carboxylate in 300 ml of acetonitrile. The reaction medium is stirred at ambient temperature for 24 h then filtered to remove the insoluble salts and concentrated under vacuum. The crude residue obtained is purified by chromatography by silica gel eluted with a 70/30 heptane/ethyl acetate mixture. 41 g (97%) of dimethyl 2-(4-tert-butoxycarbonylpiperazin-1-yl)malonate are obtained in the form of a clear oil.

Workup

  1. filtrationthen filtered
  2. customto remove the insoluble salts
  3. concentrationconcentrated under vacuum
  4. customThe crude residue obtained
  5. customis purified by chromatography by silica gel
  6. washeluted with a 70/30 heptane/ethyl acetate mixture

Sources & evidence

ORD record
ord-f2591c8401144a44ae7ed4ac1eacd7db
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

Loading…