Methanol → Methyl (3R)-3-morpholinecarboxylate

HRID 1615841Notes

Reaction equation

HRID 1615841 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]1[C:14]([OH:16])=[O:15])=O)(C)(C)C.S(Cl)(Cl)=O.[CH3:21]O>>[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][C@@H:9]1[C:14]([O:16][CH3:21])=[O:15]

Participants

4

Reactant 3

HCID 887MethanolHCID 24386Thionyl ChlorideHCID 1512538(3R)-4-(tert-Butoxycarbonyl)morpholine-3-carboxylic acid

Product 1

HCID 1514261Methyl (3R)-3-morpholinecarboxylate

Procedure

To a solution of (R)-morpholine-3,4-dicarboxylic acid-4-tert-butyl ester (5.00 g, 21.6 mmol) in MeOH (54 mL) was added thionyl chloride (3.16 mL, 43.2 mmol) dropwise, and the resulting mixture was heated at reflux for 16 h. The solution was cooled to ambient temperature and concentrated in vacuo. The residue was made basic with saturated aqueous NaHCO3 and extracted with CH2Cl2 (3×). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo to yield the title compound.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 16 h
  3. concentrationconcentrated in vacuo
  4. extractionextracted with CH2Cl2 (3×)
  5. dry with materialThe combined organic extracts were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e1981ceb9301495aae7b28aed2065113
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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