Ethylene Oxide → 2-[(3R)-3-methoxymethylmorpholino]ethanol

HRID 1765983Notes

Reaction equation

HRID 1765983 reaction equation
Cl.[CH3:2][O:3][CH2:4][C@@H:5]1[CH2:10][O:9][CH2:8][CH2:7][NH:6]1.C(N(CC)CC)C.[CH2:18]1[O:20][CH2:19]1>CO.C1(C)C=CC=CC=1>[CH3:2][O:3][CH2:4][C@H:5]1[N:6]([CH2:18][CH2:19][OH:20])[CH2:7][CH2:8][O:9][CH2:10]1

Participants

6

Reactant 3

HCID 6354Ethylene OxideHCID 8471TriethylamineHCID 53338712(3R)-3-(Methoxymethyl)morpholine--hydrogen chloride (1/1)

Product 1

HCID 538274862-[(3R)-3-methoxymethylmorpholino]ethanol

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

To a mixed solution of (3R)-3-(methoxymethyl)morpholine hydrochloride (4.71 g) and triethylamine (4.11 ml) in methanol (110 ml) was added 5.8 M ethylene oxide (22 ml) in toluene solution at room temperature. After stirring the reaction mixture at the same temperature for 2 days, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography using a mixed solvent of dichloromethane and methanol (20:1). Fractions containing the desired compound were collected and the solvent was evaporated under reduced pressure to give 2-[(3R)-3-(methoxymethyl)morpholino]ethanol (4.67 g) in the form of an oily substance.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography
  3. additionFractions containing the desired compound
  4. customwere collected
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-faa5b360b8f441e083516017d2284790
Source dataset
uspto-grants-2007_06
Patent number
US07229992B2

Reaction notes

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