HCID 67519206, compound → HCID 67519178, compound

HRID 1924438Notes

Reaction equation

HRID 1924438 reaction equation
[C:1]([O:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][C@H:14]3[N:25](C(OCC4C=CC=CC=4)=O)[CH2:24][CH2:23][C@@:20]4([C:21]=2[CH:22]=1)[C@H:15]3[CH2:16][CH2:17][CH2:18][CH2:19]4)(=[O:5])[CH:2]([CH3:4])[CH3:3]>CCO.[Pd]>[C:1]([O:6][CH2:7][O:8][C:9]1[CH:10]=[CH:11][C:12]2[CH2:13][C@H:14]3[NH:25][CH2:24][CH2:23][C@@:20]4([C:21]=2[CH:22]=1)[C@H:15]3[CH2:16][CH2:17][CH2:18][CH2:19]4)(=[O:5])[CH:2]([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 67519206HCID 67519206, compound

Product 1

HCID 67519178HCID 67519178, compoundYield 37.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(+)-[N-(Benzyloxycarbonyl)morphinan-3-yloxy]methyl isobutyrate (4.12 g, 8.63 mmol) from Example 44 was subjected to hydrogenation (balloon) on 10% Pd/C (600 mg) in EtOH (100 mL) at room temperature. After the reaction was completed, the reaction mixture was filtered through a Celite, and washed with EtOH (300 mL). The combined EtOH solution was evaporated under vacuum. The residue was further purified by reverse-phase prep HPLC to provide the title compound (1.11 g, 37%) as a light yellow gum.

Workup

  1. filtrationthe reaction mixture was filtered through a Celite
  2. washwashed with EtOH (300 mL)
  3. customThe combined EtOH solution was evaporated under vacuum
  4. customThe residue was further purified by reverse-phase prep HPLC

Sources & evidence

ORD record
ord-0c1bfdf6945742cf88bc82613201d71c
Source dataset
uspto-grants-2012_05
Patent number
US08178551B2

Reaction notes

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