Methanol → (+/-)-trans-3-Methyl norfentanyl

HRID 2051517Notes

Reaction equation

HRID 2051517 reaction equation
C(OC([N:11]1[CH2:16][CH2:15][C@@H:14]([N:17]([C:24](=[O:27])[CH2:25][CH3:26])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C@H:13]([CH3:28])[CH2:12]1)=O)C1C=CC=CC=1.CO>[Pd].C(O)(=O)C>[CH3:28][C@H:13]1[C@H:14]([N:17]([C:24](=[O:27])[CH2:25][CH3:26])[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH2:15][CH2:16][NH:11][CH2:12]1

Participants

5

Reactant 2

HCID 887MethanolHCID 14987178HCID 14987178, compound

Product 1

HCID 14969498(+/-)-trans-3-Methyl norfentanyl

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of trans-N-benzyloxycarbonyl-3-methyl-4-[(1-oxopropyl)phenylamino]-piperidine (1.5 g, 3.94 mmol), 10% Pd-C (200 mg), methanol (20 ml), and acetic acid (20 ml) is hydrogenated at 50 psi for 24 hours. The resultant suspension is filtered through a bed of Celite and the filtrate concentrated. The residue is diluted with ethyl acetate (50 ml), basified to pH 11 with 2N NaOH and shaken. The organic layer is separated, dried over magnesium sulfate, and concentrated to trans-3-methyl-4-[(1-oxopropyl)-phenylamino]-piperidine: 720 mg; 96%.

Workup

  1. filtrationThe resultant suspension is filtered through a bed of Celite
  2. concentrationthe filtrate concentrated
  3. additionThe residue is diluted with ethyl acetate (50 ml)
  4. customThe organic layer is separated
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated to trans-3-methyl-4-[(1-oxopropyl)-phenylamino]-piperidine

Sources & evidence

ORD record
ord-da1dd493f8a7464c9f712955394115f3
Source dataset
uspto-grants-1991_05
Patent number
US05019583

Reaction notes

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