Water → HCID 90043292, compound

HRID 524662Notes

Reaction equation

HRID 524662 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[CH2:7]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH:15]1[CH2:20][CH:21]([C:27](OCC)=[O:28])[C:22](OCC)=[O:23])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C1COCC1>[CH2:7]([N:14]1[CH2:19][CH2:18][O:17][CH2:16][CH:15]1[CH2:20][CH:21]([CH2:27][OH:28])[CH2:22][OH:23])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 90043982HCID 90043982, compound

Product 1

HCID 90043292HCID 90043292, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
30 °C

Procedure

LiAlH4 (0.35 g, 9.32 mmol) in a dried flask was cooled to 0° C., and then anhydrous THF (15 mL) was added. The mixture was stirred thoroughly and a solution of diethyl 2-((4-benzylmorpholin-3-yl)methyl)malonate (0.93 g, 2.66 mmol) in anhydrous THF (5 mL) was added, then the mixture was stirred at 70° C. for 6 hours and cooled to 30° C. To the reaction mixture were added water (0.5 mL), sodium hydroxide aqueous solution (10%, 0.5 mL) and water (3 mL) in turn, then the mixture was stirred at 25° C. for 10 minutes and filtered. The filtrate was concentrated in vacuo and the residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=3/1) to give the title compound as colorless oil (0.38 g, 54%). The compound was characterized by the following spectroscopic data:

Workup

  1. stirringthe mixture was stirred at 70° C. for 6 hours
  2. stirringthe mixture was stirred at 25° C. for 10 minutes
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by a silica gel column chromatography (PETROLEUM ETHER/EtOAc (V/V)=3/1)

Sources & evidence

ORD record
ord-3834c29862924f60aad0deeeca2072fa
Source dataset
uspto-grants-2016_05
Patent number
US09340538B2

Reaction notes

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