Methyl propiolate → HCID 58996700, compound

HRID 1592743Notes

Reaction equation

HRID 1592743 reaction equation
[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][N:21]=[N+:22]=[N-:23])[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[C:24]([O:28][CH3:29])(=[O:27])[C:25]#[CH:26]>>[C:1]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH2:20][N:21]2[CH:26]=[C:25]([C:24]([O:28][CH3:29])=[O:27])[N:23]=[N:22]2)[CH2:10][CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

3

Reactant 2

HCID 13536Methyl propiolateHCID 17952251HCID 17952251, compound

Product 1

HCID 58996700HCID 58996700, compoundYield 49%

Procedure

1-Boc-4-(2-Azidomethyl-phenyl)-piperazine (0.25 g, 0.79 mmol) was dissolved in deuterated chloroform (3 mL). Methyl propiolate (0.35 mL, 3.9 mmol) was added, and the mixture was heated to reflux for about 4 hours and then cooled to r.t. The mixture was concentrated under reduced pressure and purified using silica chromatography (50% ethyl acetate in hexanes) to give the title compound (0.155 g, 49%) as an oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for about 4 hours
  3. concentrationThe mixture was concentrated under reduced pressure
  4. custompurified

Sources & evidence

ORD record
ord-5301fff6e0a24329a6eb1deab3d65b05
Source dataset
uspto-grants-2007_11
Patent number
US07291619B2

Reaction notes

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