Methanol → Methyl 4-aminooxane-4-carboxylate hydrochloride

HRID 383536

Reaction equation

HRID 383536 reaction equation
S(Cl)([Cl:3])=O.Cl.[NH2:6][C:7]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1.[CH3:16]O>>[ClH:3].[NH2:6][C:7]1([C:13]([O:15][CH3:16])=[O:14])[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 27344004-Aminotetrahydro-2H-pyran-4-carboxylic acid hydrochloride

Product 1

HCID 43811077Methyl 4-aminooxane-4-carboxylate hydrochloride

Procedure

Thionyl chloride (4.02 mL, 55.1 mmol) was added in the dehydrated methanol (100 mL) solution of 4-amino-4-carboxytetrahydro-pyran monohydrochloride (5.00 g, 27.5 mmol) in an ice bath, and the mixture was heated and refluxed for 2.5 hours. The solvent was removed by distillation under reduced pressure, and the obtained crude product was washed with ethyl acetate and then dried under reduced pressure to give a colorless solid (BB04, 5.06 g).

Workup

  1. temperaturethe mixture was heated
  2. temperaturerefluxed for 2.5 hours
  3. customThe solvent was removed by distillation under reduced pressure
  4. customthe obtained crude product
  5. washwas washed with ethyl acetate
  6. customdried under reduced pressure
  7. customto give a colorless solid (BB04, 5.06 g)

Sources & evidence

ORD record
ord-caa6434e25514b198f46e5a096eb539c
Source dataset
uspto-grants-2013_02
Patent number
US08367666B2

Linked notes

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