Ethyl Acetate → HCID 59401367, compound

HRID 2060874Notes

Reaction equation

HRID 2060874 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([OH:10])=O)[CH2:3][CH2:2]1.Cl.[CH3:12][NH2:13].[OH-].[Na+].CCOC(C)=O>S(Cl)(Cl)=O.CN(C=O)C.O>[CH3:12][NH:13][C:8](=[O:10])[CH2:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1

Participants

8

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 2773575Tetrahydropyran-4-ylacetic acidHCID 6364545Methylamine hydrochloride

Product 1

HCID 59401367HCID 59401367, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 962WaterSolventHCID 24386Thionyl ChlorideSolvent

Procedure

To a solution of (tetrahydropyran-4-yl)acetic acid (500 mg, 3.47 mmol) in thionyl chloride (10 mL) was added DMF (1 drop). The reaction was heated to reflux for 1 h, cooled to rt and the solvent removed in vacuo. The residue was redissolved in THF (5 mL) and added dropwise to a solution of methylamine hydrochloride (2.34 g, 34.7 mmol) and NaOH (1.11 g, 27.7 mmol) in water. The solution was stirred for 30 min and EtOAc (100 mL) added. The mixture was extracted with EtOAc (5×100 mL) and the combined organic phase dried (MgSO4). Solvent was removed in vacuo to give the title compound: δH (CDCl3) 1.14-1.33 (2H, m), 1.48-1.63 (3H, m), 1.97-2.07 (2H, m), 2.74 (3H, s), 3.26-3.41 (2H, m), 3.87 (2H, dd), 5.34 (1H, bs).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 1 h
  3. customthe solvent removed in vacuo
  4. dissolutionThe residue was redissolved in THF (5 mL)
  5. extractionThe mixture was extracted with EtOAc (5×100 mL)
  6. dry with materialthe combined organic phase dried (MgSO4)
  7. customSolvent was removed in vacuo

Sources & evidence

ORD record
ord-66007f3ffd0b454aa8c618cda74932da
Source dataset
uspto-grants-2012_10
Patent number
US08278442B2

Reaction notes

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