Methyl acetoacetate → HCID 86714185, compound

HRID 920078Notes

Reaction equation

HRID 920078 reaction equation
[CH:1]1([CH2:6][NH2:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:8][O:9][C:10](=[O:15])[CH2:11][C:12](=O)[CH3:13].[CH3:16][O:17][C:18](=[O:21])[C:19]#[CH:20]>CO>[CH3:16][O:17][C:18](=[O:21])[CH:19]=[CH:20][C:11](=[C:12]([NH:7][CH2:6][CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)[CH3:13])[C:10]([O:9][CH3:8])=[O:15]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 13536Methyl propiolateHCID 80153Cyclopentanemethylamine

Product 1

HCID 86714185HCID 86714185, compoundYield 55.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of cyclopentanemethylamine (4.52 g, 45.7 mmol) and 3-oxo-butyric acid methyl ester (5.9 mL, 54.8 mmol) in MeOH (170 mL) was refluxed for 2 h. Propynoic acid methyl ester (6.1 mL, 68.5 mmol) was added, and the resulting mixture was refluxed for 2 days. After cooling to r.t., the solvent was evaporated, and the residue was recrystallized from MeOH to give 7.17 g of the title compound as a light tan solid. MS: (+) m/z 282.33 (M+1).

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturethe resulting mixture was refluxed for 2 days
  3. customthe solvent was evaporated
  4. customthe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-5651338d8501402ba576f7f82c06afb0
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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