3,4-dihydro-2H-pyran → HCID 14978394, compound

HRID 1489421Notes

Reaction equation

HRID 1489421 reaction equation
[OH:1][C@@H:2]([CH3:11])[C:3]([N:5]1[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].[O:12]1[CH:17]=[CH:16][CH2:15][CH2:14][CH2:13]1>ClCCl.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>[O:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH:13]1[O:1][C@@H:2]([CH3:11])[C:3]([N:5]1[CH2:6][CH2:7][O:8][CH2:9][CH2:10]1)=[O:4]

Participants

5

Reactant 2

HCID 80803,4-dihydro-2H-pyranHCID 11062669HCID 11062669, compound

Product 1

HCID 14978394HCID 14978394, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 69.4 g of 4-[(S)-2-hydroxypropionyl]-morpholine in 300 ml of dichloromethane was added 0.82 g of p-toluenesulfonic acid monohydrate, to which 40.3 g of 3,4-dihydro-2H-pyran was added dropwise with ice cooling. The reaction solution was stirred at 0° C. for 30 minutes and washed with an aqueous solution of 5% sodium bicarbonate. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=8:1 to ethyl acetate) to give 89.1 g of 4-[(2S)-2-(3,4,5,6-tetrahydro-2H-pyran-2-yloxy)propionyl]morpholine as a pale yellow oil.

Workup

  1. washwashed with an aqueous solution of 5% sodium bicarbonate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=8:1 to ethyl acetate)

Sources & evidence

ORD record
ord-3ef6915724884f1d883b085aba221725
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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