Sodium hydride → HCID 20139873, compound

HRID 1252513Notes

Reaction equation

HRID 1252513 reaction equation
Br[CH:2]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:3]([NH:5][CH:6]([CH2:11][OH:12])[CH2:7][CH:8]([CH3:10])[CH3:9])=[O:4].[H-].[Na+]>O1CCCC1>[CH3:9][CH:8]([CH3:10])[CH2:7][CH:6]1[NH:5][C:3](=[O:4])[CH:2]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:12][CH2:11]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 20139848HCID 20139848, compound

Product 1

HCID 20139873HCID 20139873, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

α-Bromo-N-[(1-hydroxymethyl)-3-methylbutyl]benzeneacetamide (α-center is RS, other center with NH-substituent is S), 9.1 g (0.029 mole), was dissolved in 200 ml of tetrahydrofuran, the solution is cooled to 0°-5° and 1.65 g (0.0413 mole) of 60% sodium hydride in mineral oil dispersion slowly added. The mixture was allowed to reach room temperature and stirred overnight, the solvent was evaporated in vacuo and the residue dissolved in 200 ml of dichloromethane and extracted twice with water. The dichloromethane layer was separated, dried over sodium sulfate, evaporated in vacuo and the residue chromatographed using 200 g of silica gel and eluting with 1 l of dichloromethane-methanol (99.5:0.5) to give 5-(2-methylpropyl)-2-phenyl-3-morpholinone (center phenyl is R, S, other center is S), 5.48 g; [α]D25 =-22.9° (C, 0.62, methanol).

Workup

  1. temperaturethe solution is cooled to 0°-5°
  2. customto reach room temperature
  3. customthe solvent was evaporated in vacuo
  4. dissolutionthe residue dissolved in 200 ml of dichloromethane
  5. extractionextracted twice with water
  6. customThe dichloromethane layer was separated
  7. dry with materialdried over sodium sulfate
  8. customevaporated in vacuo
  9. customthe residue chromatographed
  10. washeluting with 1 l of dichloromethane-methanol (99.5:0.5)

Sources & evidence

ORD record
ord-04fabb118fc04eec89b80320f6c1fdd9
Source dataset
uspto-grants-1988_05
Patent number
US04743585

Reaction notes

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