4-Aminotetrahydro-2H-pyran-4-carboxylic acid hydrochloride → Methyl 4-aminooxane-4-carboxylate

HRID 1409549

Reaction equation

HRID 1409549 reaction equation
Cl.[NH2:2][C:3]1([C:9]([OH:11])=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[CH3:12][Si](C=[N+]=[N-])(C)C.C(OCC)C>CO>[NH2:2][C:3]1([C:9]([O:11][CH3:12])=[O:10])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

4

Reactant 2

HCID 27344004-Aminotetrahydro-2H-pyran-4-carboxylic acid hydrochlorideHCID 23159941trimethylsilyldiazomethane Et2O

Product 1

HCID 18698314Methyl 4-aminooxane-4-carboxylateYield 99%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-amino-4-carboxy-tetrahydropyrane hydrochloride (2 g) in methanol was added dropwise a solution of 2M trimethylsilyldiazomethane-diethylether (33 mL) under ice-cooling, and the mixture was stirred at room temperature for 4 days. The reaction mixture was concentrated in vacuo, and the resultant crude product was dissolved in hexane-diethylether (1 mL/1 mL), and thereto was added an aqueous 4N hydrochloric acid. The precipitates were collected by filtration to give 4-amino-4-methoxycarbonyl-tetrahydropyrane (2.13 g, yield: 99%) as white crystals.

Workup

  1. temperaturecooling
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. dissolutionthe resultant crude product was dissolved in hexane-diethylether (1 mL/1 mL)
  4. additionwas added an aqueous 4N hydrochloric acid
  5. filtrationThe precipitates were collected by filtration

Sources & evidence

ORD record
ord-c6845010739e41f19e1c9c8429a37b52
Source dataset
uspto-grants-2014_12
Patent number
US08921380B2

Linked notes

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