Ammonium Hydroxide → (-)-3-acetyl-N-methylmorphinan

HRID 1758500Notes

Reaction equation

HRID 1758500 reaction equation
C([C@H]([C@@H](C(O)=O)O)O)(O)=O.[C:11]([C:14]1[CH:15]=[CH:16][C:17]2[CH2:18][C@H:19]3[N:30]([CH3:31])[CH2:29][CH2:28][C@@:25]4([C:26]=2[CH:27]=1)[C@H:20]3[CH2:21][CH2:22][CH2:23][CH2:24]4)(=[O:13])[CH3:12].[OH-].[NH4+]>O>[C:11]([C:14]1[CH:15]=[CH:16][C:17]2[CH2:18][C@H:19]3[N:30]([CH3:31])[CH2:29][CH2:28][C@@:25]4([C:26]=2[CH:27]=1)[C@H:20]3[CH2:21][CH2:22][CH2:23][CH2:24]4)(=[O:13])[CH3:12]

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 13100582(-)-3-Acetyl-N-methylmorphinan d-tartrate

Product 1

HCID 13100578(-)-3-acetyl-N-methylmorphinanYield 99%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

(-)-3-Acetyl-N-methylmorphinan d-tartrate, 4.30 g was suspended in 20 ml water and made basic with concentrated ammonium hydroxide. The resulting suspension was extracted with ether (2×40 ml). The ether extracts were washed with water and dried over magnesium sulfate. Removal of the solvent gave 2.8 g (99%) of (-)-3-acetyl-N-methylmorphinan. For analysis, a sample of this compound was distilled, bp 175°-185° (0.2 mm), [α]25D-47.14° (c 1.17, MeOH).

Workup

  1. extractionThe resulting suspension was extracted with ether (2×40 ml)
  2. washThe ether extracts were washed with water
  3. dry with materialdried over magnesium sulfate
  4. customRemoval of the solvent

Sources & evidence

ORD record
ord-cd8a52bed9024922a127b1565ad84750
Source dataset
uspto-grants-1983_02
Patent number
US04374139

Reaction notes

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