Methanol → Methyl 3-Morpholinecarboxylate
Reaction equation
Cl.[NH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[C:8]([OH:10])=[O:9].S(Cl)(Cl)=O.[CH3:15]O>>[NH:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[C:8]([O:10][CH3:15])=[O:9]Participants
4
Conditions
- Temperature
- -20 °C
Procedure
Morpholine-3-carboxylic acid hydrochloride (1.04 g) was dissolved in methanol (20 ml) and the solution cooled to -20° C. Thionyl chloride (1 ml) was added dropwise to the stirred reaction mixture such that the temperature did not rise above -10°. After the addition was complete the reaction mixture was stirred at room temperature for 16 h. The solvent was removed in vacuo and the resultant pale grey residue was partitioned between 2N Na2CO3 and dichloromethane. The organic phase was separated, dried, and the solvent was removed in vacuo to give the title compound as an oil (220 mg).
Workup
- customdid not rise above -10°
- additionAfter the addition
- customThe solvent was removed in vacuo
- customthe resultant pale grey residue was partitioned between 2N Na2CO3 and dichloromethane
- customThe organic phase was separated
- customdried
- customthe solvent was removed in vacuo
Sources & evidence
- ORD record
- ord-6ca88673f4a8479ba37ac558ea48ddd5
- Source dataset
- uspto-grants-1990_05
- Patent number
- US04923863
Reaction notes
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