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

HRID 1374976Notes

Reaction equation

HRID 1374976 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 5.8M ethylene oxide (22 ml) in toluene solution at room temperature. After the reaction mixture was stirred at the same temperature for two days, it was evaporated under reduced pressure. The residue was purified by column chromatography on silica gel using mixed solvents of dichloromethane and methanol (20:1). The fractions containing the objective compound were collected and evaporated under reduced pressure to give 2-[(3R)-3-methoxymethylmorpholino]ethanol (4.67 g) as an oil.

Workup

  1. customit was evaporated under reduced pressure
  2. customThe residue was purified by column chromatography on silica gel using
  3. additionmixed solvents of dichloromethane and methanol (20:1)
  4. additionThe fractions containing the objective compound
  5. customwere collected
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-8b950683a79e4a3fbb2937c07e4313a1
Source dataset
uspto-grants-2007_01
Patent number
US07166598B2

Reaction notes

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