Ethyl Acetate → HCID 14356857, compound

HRID 1669740Notes

Reaction equation

HRID 1669740 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][C:5](=O)[N:4]([CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C.S([O-])([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[CH3:1][C:2]1([CH3:17])[CH2:7][CH2:6][CH2:5][N:4]([CH2:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH2:3]1

Participants

6

Reactant 4

HCID 8857Ethyl Acetate2×HCID 24436Sodium SulfateHCID 13462174HCID 13462174, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 14356857HCID 14356857, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
27.5 °C

Procedure

A solution of 3,3-dimethyl-1-(phenylmethyl)-2,6-piperidinedione (200 g) in THF (400 ml) is added over 1-4 h (for example 1-2 h) at −5 to +5° C. to a solution of lithium aluminium hydride (68 g) in THF (2 L). The mixture is then heated to 20-35° C. for about 1-2 h, and then to reflux for 24-30 h. The mixture is then cooled to −5 to +5° C. and ethyl acetate (280 ml) is added slowly, followed by aqueous sodium sulphate (257 g in water 1.4 L) and further ethyl acetate (1 L). The mixture is stirred at 25-35° C. for about 1 h. The organic layer is filtered through a Hyflow bed, washing with ethyl acetate (2×2 L). The filtrate layers are combined, then washed with brine (1 L) and evaporated to give the product. The product may be further purified by column chromatography, eluting with petroleum ether and ethyl acetate mixtures or by fractional distillation (dry weight 105 g).

Workup

  1. temperatureto reflux for 24-30 h
  2. temperatureThe mixture is then cooled to −5 to +5° C.
  3. filtrationThe organic layer is filtered through a Hyflow bed
  4. washwashing with ethyl acetate (2×2 L)
  5. washwashed with brine (1 L)
  6. customevaporated
  7. customto give the product
  8. customThe product may be further purified by column chromatography
  9. washeluting with petroleum ether and ethyl acetate mixtures or by fractional distillation (dry weight 105 g)

Sources & evidence

ORD record
ord-853be0aee9a34ea7878bc0681cb861e8
Source dataset
uspto-grants-2011_08
Patent number
US07989629B2

Reaction notes

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