Water → HCID 15572608, compound

HRID 903962Notes

Reaction equation

HRID 903962 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[Na].[OH:8][C:9]([CH:14]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])=[CH:10][N+:11]([O-])=O.O.[OH-].[Na+]>O1CCCC1>[OH:8][CH:9]([CH:14]([O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[O:22][CH3:23])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[CH2:10][NH2:11]

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 70579319HCID 70579319, compound

Product 1

HCID 15572608HCID 15572608, compoundYield 47.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 0.55 g of LiAlH4 in 18 ml of anhydrous tetrahydrofuran there was added dropwise at 30° C. over 4 hours 1 g of 2-hydroxy-1-nitro-3-phenyl-3-(2-methoxy-phenoxy)-propene sodium salt in 70 ml of anhydrous tetrahydrofuran. After the addition, the mixture was cooled and decomposed with water, 15% NaOH, water. It was then filtered; the solid was washed with tetrahydrofuran and the solvent evaporated to dryness. The residue was dissolved in ethyl ether and extracted with 3% HCl, made alkaline with 20% NaOH NaOH and re-extracted with ethyl ether. The organic solution was then washed with water, dried over Na2SO4, filtered and evaporated to dryness. A small quantity of isopropyl ether was then used to ground it to obtain 2-hydroxy-3-(2-methoxy-phenoxy)-3-phenyl-propylamine (0.4 g); melting point 84°-110° C. (R=47.2%) as mixture of two diastereoisomers. The mixture was separated by column chromatography on silica gel (phase: CHCl3 /CH 3 OH/32% NH4OH-150/50/2) to obtain two distinct diastereoisomers having melting point of 126°-129° C. (diastereoisomer with Rf<) and 105°-110° C. respectively (diastereoisomer with Rf>)

Workup

  1. additionAfter the addition
  2. temperaturethe mixture was cooled
  3. filtrationIt was then filtered
  4. washthe solid was washed with tetrahydrofuran
  5. customthe solvent evaporated to dryness
  6. dissolutionThe residue was dissolved in ethyl ether
  7. extractionextracted with 3% HCl
  8. extractionre-extracted with ethyl ether
  9. washThe organic solution was then washed with water
  10. dry with materialdried over Na2SO4
  11. filtrationfiltered
  12. customevaporated to dryness

Sources & evidence

ORD record
ord-1bceb13111054c3a80a08bca569db54d
Source dataset
uspto-grants-1980_10
Patent number
US04229449

Reaction notes

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