Morpholine → (R)-2-Hydroxy-1-morpholinopropan-1-one

HRID 379655

Reaction equation

HRID 379655 reaction equation
[C:1]([O:6]C)(=O)[C@@H:2]([CH3:4])[OH:3].[NH:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1>C(OCC)(=O)C>[OH:3][C@H:2]([CH3:4])[C:1]([N:8]1[CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)=[O:6]

Participants

4

Reactant 2

HCID 8083MorpholineHCID 637514(+)-Methyl lactate

Product 1

HCID 14978393(R)-2-Hydroxy-1-morpholinopropan-1-oneYield 87%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of methyl (R)-lactate (175 g) and morpholine (440 ml, 3 eq) was heated at 85° C. for 40 h. The mixture was evaporated under reduced pressure. Purification of the residue by silica gel chromatography (using n-hexane:ethyl acetate=1:1 ˜ethyl acetate as an eluent) gave 4-[(R)-2-hydroxypropionyl]morpholine (232.4 g, 87% yield) as a pale yellow oil.

Workup

  1. customThe mixture was evaporated under reduced pressure
  2. customPurification of the residue by silica gel chromatography (

Sources & evidence

ORD record
ord-94c4aacdfda3451caec808415054f4a0
Source dataset
uspto-grants-2001_10
Patent number
US06300353B1

Linked notes

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