Water → HCID 15942836, compound

HRID 1701581Notes

Reaction equation

HRID 1701581 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C1(C2C=[CH:15][C:16]3[CH2:17][C@H:18]4[N:29]([CH:30]=O)[CH2:28][CH2:27][C@@:24]5([C:25]=3[CH:26]=2)[C@H:19]4[CH2:20][CH2:21][CH2:22][CH2:23]5)C=CC=CC=1.[C:32]([O:35][CH2:36][CH3:37])(=O)[CH3:33].O>O1CCCC1>[O:35]([C:36]1[CH:37]=[CH:15][C:16]2[CH2:17][C@H:18]3[N:29]([CH3:30])[CH2:28][CH2:27][C@@:24]4([C:25]=2[CH:26]=1)[C@H:19]3[CH2:20][CH2:21][CH2:22][CH2:23]4)[C:32]1[CH:24]=[CH:25][CH:16]=[CH:15][CH:33]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydrideHCID 22810375HCID 22810375, compound

Product 1

HCID 15942836HCID 15942836, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 1.1 g of lithium aluminum hydride in 120 ml of anhydrous tetrahydrofuran, 10.8 g (0.03 mol) of crude (±)-3-phenyl-N-formylmorphinan in 50 ml of tetrahydrofuran was added dropwise. After the mixture had been refluxed for 3 hrs, it was cooled to room temperature and ethyl acetate followed by water were added dropwise. The resulting suspension was dried, filtered and the filtrate concentrated in vacuo to give a dark brown oil which was distilled, bp 170°-180° (0.05 mm Hq) to afford 7.6 g (73%) of crude (±)-3-phenoxy-N-methylmorphinan.

Workup

  1. additionwas added dropwise
  2. temperatureAfter the mixture had been refluxed for 3 hrs
  3. additionwere added dropwise
  4. customThe resulting suspension was dried
  5. filtrationfiltered
  6. concentrationthe filtrate concentrated in vacuo
  7. customto give a dark brown oil which
  8. distillationwas distilled

Sources & evidence

ORD record
ord-e4a6c7c23e6749699e9b1bddb07a5740
Source dataset
uspto-grants-1980_03
Patent number
US04194044

Reaction notes

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