Morphine → Dihydromorphine

HRID 2185871Notes

Reaction equation

HRID 2185871 reaction equation
[CH:1]1[C:17]2[CH2:16][C@H:15]3[N:18]([CH2:20][CH2:21][C@@:7]45[C@H:14]3[CH:13]=[CH:12][C@H:10]([OH:11])[C@@H:8]4[O:9][C:5]([C:6]=25)=[C:3]([OH:4])[CH:2]=1)[CH3:19].C(Cl)(Cl)Cl.CO>C(O)C>[CH3:19][N:18]1[C@@H:15]2[CH2:16][C:17]3[CH:1]=[CH:2][C:3]([OH:4])=[C:5]4[O:9][C@H:8]5[C@@H:10]([OH:11])[CH2:12][CH2:13][C@@H:14]2[C@:7]5([C:6]=34)[CH2:21][CH2:20]1

Participants

4

Reactant 2

HCID 5288826MorphineHCID 21584188Chloroform methanol

Product 1

HCID 5359421Dihydromorphine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To morphine free base (3 am, 10.5 mmol.) dissolved in absoTute ethanol (150 ml) palladium-on-activated carbon (5˜o) (1 am., 50 p.s.i.) was added. Reduction was carried out overnight (12-14 hours), in a Parr hydrogenator at ambient temperature. After confirmation of the quantitative conversion to 7,8-dihydromorphine by TLC, the ethanolic solution was filtered over Celite. The organic solvent ethanol was removed by rotary evaporation at reduced pressure, to afford 2.93 am. (97.2%) of dibydromorphine as an off-white glassy solid, homogeneous by TLC (CHCl3:MeOH (9:1), Rf=0.2). Elemental Analysis Calcd. for C17H21NO3:C, 71.08; H, 7.32; N, 4.88. Found: C, 71.11; H, 7.34; N, 4.91.

Workup

  1. additionwas added
  2. custom(12-14 hours)
  3. customat ambient temperature
  4. filtrationAfter confirmation of the quantitative conversion to 7,8-dihydromorphine by TLC, the ethanolic solution was filtered over Celite
  5. customThe organic solvent ethanol was removed by rotary evaporation at reduced pressure
  6. customto afford 2.93

Sources & evidence

ORD record
ord-daeb21f2dacf4d66bf42d68acb75b9cb
Source dataset
uspto-grants-2002_06
Patent number
US06403602B1

Reaction notes

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