Methanol → Methyl (3R)-3-morpholinecarboxylate
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
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
- temperaturethe resulting mixture was heated
- temperatureat reflux for 16 h
- concentrationconcentrated in vacuo
- extractionextracted with CH2Cl2 (3×)
- dry with materialThe combined organic extracts were dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-e1981ceb9301495aae7b28aed2065113
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08765759B2
Reaction notes
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