Water → HCID 16244204, compound

HRID 1859030Notes

Reaction equation

HRID 1859030 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[C:6](=[N:12]O)[CH2:5]2.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>O1CCCC1>[NH2:12][CH:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([F:1])[CH:3]=2)[CH:7]1[OH:11]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 56723947HCID 56723947, compound

Product 1

HCID 16244204HCID 16244204, compoundYield 46%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

The product obtained in Step A dissolved in 70 ml of tetrahydrofuran is added dropwise, in the course of 30 minutes, to a suspension of 2.67 g of lithium aluminium hydride in 15 ml of tetrahydrofuran. After stirring for 30 minutes at ambient temperature and then after 12 hours at reflux of the solvent, the reaction mixture is cooled and then carefully hydrolysed using, in succession, 1.9 ml of water, 1.5 ml of 20% sodium hydroxide solution and then 6.7 ml of water. The solution is subsequently stirred for 3 hours at ambient temperature and then filtered, rinsed with tetrahydrofuran and evaporated to dryness. Chromatography on silica gel (dichloromethane/methanol/ammonium hydroxide: 95/5/0.5) allows the expected product to be isolated in the proportion of 54% of the cis product and 46% of the trans product.

Workup

  1. temperatureafter 12 hours at reflux of the solvent
  2. temperaturethe reaction mixture is cooled
  3. stirringThe solution is subsequently stirred for 3 hours at ambient temperature
  4. filtrationfiltered
  5. washrinsed with tetrahydrofuran
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-6dbff62d0713461da76080a63f39713a
Source dataset
uspto-grants-2000_11
Patent number
US06153625

Reaction notes

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