Methyl acetoacetate → HCID 86714154, compound

HRID 919934Notes

Reaction equation

HRID 919934 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[CH3:9][O:10][C:11](=[O:16])[CH2:12][C:13](=O)[CH3:14].[CH3:17][O:18][C:19](=[O:22])[C:20]#[CH:21]>CO>[CH3:17][O:18][C:19](=[O:22])[CH:20]=[CH:21][C:12](=[C:13]([NH:1][CH2:2][CH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1)[CH3:14])[C:11]([O:10][CH3:9])=[O:16]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 13536Methyl propiolateHCID 27732104-Aminomethyltetrahydropyran

Product 1

HCID 86714154HCID 86714154, compoundYield 90.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-aminomethyltetrahydropyran (1.02 g, 8.9 mmol) and 3-oxo-butyric acid methyl ester (1.15 mL, 10.6 mmol) in MeOH (40 mL) was refluxed for 2 h. Propynoic acid methyl ester (1.2 mL, 13.3 mmol) was added, and the resulting mixture was refluxed for 48 h. After cooling to r.t., the solvent was evaporated, and the crude oil was recrystallized from MeOH to give 2.39 g of the title compound as an off-white solid. MS: (+) m/z 298.33 (M+1).

Workup

  1. temperaturewas refluxed for 2 h
  2. temperaturethe resulting mixture was refluxed for 48 h
  3. customthe solvent was evaporated
  4. customthe crude oil was recrystallized from MeOH

Sources & evidence

ORD record
ord-d4de8756353049f5b9def7f614170256
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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