Sodium Hydroxide → HCID 18949782, compound

HRID 1492902Notes

Reaction equation

HRID 1492902 reaction equation
[N+:1]([CH:4]([CH3:22])[CH:5]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=1)[CH2:6][C:7](OCC)=[O:8])([O-])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.C1COCC1.[OH-].[Na+]>C(OCC)C>[C:18]([C:15]1[CH:14]=[CH:13][C:12]([CH:5]([CH:4]([NH2:1])[CH3:22])[CH2:6][CH2:7][OH:8])=[CH:17][CH:16]=1)([CH3:21])([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 18949785Ethyl 4-(1,1-dimethylethyl)-β-(1-nitroethyl)benzenepropanoateHCID 21226445Aluminium lithium hydrideHCID 21881883Oxolane--water (1/1)

Product 1

HCID 18949782HCID 18949782, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

6.5 g (0.021 mol) of the nitro ester prepared as in (b) above was added dropwise to 5 g (0.18 mol) of lithium aluminum hydride suspended in 200 mL of anhydrous diethyl ether, under nitrogen with stirring. The mixture was then refluxed for ten hours. A 50 percent H2O/THF solution was added dropwise and slowly with vigorous stirring until effervescence ceased. 1N sodium hydroxide solution was then added dropwise until the slurry coagulated to a coarse sandy consistency. The mixture was filtered and the solid washed with diethyl ether. The organic fractions were combined, washed with water, dried, filtered and the solvent evaporated off at reduced pressure to afford 4 g (80 percent of theoretical) of the crude product in the form of a gum. The NMR and IR spectra of the product were consistent with the expected structure, and indicated a mixture of the two possible diastereoisomers in a ratio of 2:1.

Workup

  1. temperatureThe mixture was then refluxed for ten hours
  2. stirringslowly with vigorous stirring until effervescence
  3. filtrationThe mixture was filtered
  4. washthe solid washed with diethyl ether
  5. washwashed with water
  6. customdried
  7. filtrationfiltered
  8. customthe solvent evaporated off at reduced pressure

Sources & evidence

ORD record
ord-e02c04289135438b9a4e21ec3d4cc55a
Source dataset
uspto-grants-1994_12
Patent number
US05376659

Reaction notes

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