(5S)-4-[(4-Methoxyphenyl)methyl]-5-methylmorpholin-3-one → HCID 59525840, compound

HRID 385767Notes

Reaction equation

HRID 385767 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:23]=[CH:22][C:12]([CH2:13][N:14]2[C@@H:19]([CH3:20])[CH2:18][O:17][CH2:16][C:15]2=O)=[CH:11][CH:10]=1>C1COCC1>[CH3:7][O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[CH2:15][CH2:16][O:17][CH2:18][C@@H:19]2[CH3:20])=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 15225767(5S)-4-[(4-Methoxyphenyl)methyl]-5-methylmorpholin-3-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 59525840HCID 59525840, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

Into a 5000 mL 4-necked, round bottomed flask purged and maintained with an inert atmosphere of nitrogen was placed a suspension of lithium aluminum hydride (60.04 g, 1.58 mol) in THF (2000 mL), followed by the dropwise addition of a solution of (S)-4-(4-methoxybenzyl)-5-methylmorpholin-3-one (186 g, 790.48 mmol) in THF (300 mL). The resulting solution was heated to reflux for 1 hour. The reaction mixture was cooled to 0° C., quenched by adding 500 mL of ethyl acetate and then 500 mL of water, the resulting solution was extracted three times with 2000 mL of ethyl acetate. The combined organic layer was dried over MgSO4, filtered, and concentrated under vacuum. The residue was purified by flash chromatography (silica, 1:30 ethyl acetate/petroleum ether) to afford the title compound as a yellow oil.

Workup

  1. customInto a 5000 mL 4-necked, round bottomed flask purged
  2. temperaturemaintained with an inert atmosphere of nitrogen
  3. temperatureThe resulting solution was heated
  4. temperatureto reflux for 1 hour
  5. customquenched
  6. additionby adding 500 mL of ethyl acetate
  7. extraction500 mL of water, the resulting solution was extracted three times with 2000 mL of ethyl acetate
  8. dry with materialThe combined organic layer was dried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum
  11. customThe residue was purified by flash chromatography (silica, 1:30 ethyl acetate/petroleum ether)

Sources & evidence

ORD record
ord-6365588d1af3408ca3a37fe3b2dce98e
Source dataset
uspto-grants-2013_02
Patent number
US08367706B2

Reaction notes

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