(+)-[N-(Benzyloxycarbonyl)morphinan-3-yloxy]methyl pivalate → (+)-(Morphinan-3-yloxy)methyl pivalate

HRID 1924440Notes

Reaction equation

HRID 1924440 reaction equation
[C:1]([O:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[CH2:14][C@H:15]3[N:26](C(OCC4C=CC=CC=4)=O)[CH2:25][CH2:24][C@@:21]4([C:22]=2[CH:23]=1)[C@H:16]3[CH2:17][CH2:18][CH2:19][CH2:20]4)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]>CCO.[Pd]>[C:1]([O:7][CH2:8][O:9][C:10]1[CH:11]=[CH:12][C:13]2[CH2:14][C@H:15]3[NH:26][CH2:25][CH2:24][C@@:21]4([C:22]=2[CH:23]=1)[C@H:16]3[CH2:17][CH2:18][CH2:19][CH2:20]4)(=[O:6])[C:2]([CH3:5])([CH3:4])[CH3:3]

Participants

4

Reactant 1

HCID 67519183(+)-[N-(Benzyloxycarbonyl)morphinan-3-yloxy]methyl pivalate

Product 1

HCID 67519159(+)-(Morphinan-3-yloxy)methyl pivalateYield 45%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

(+)-[N-(Benzyloxycarbonyl)morphinan-3-yloxy]methyl pivalate (13.2 g, 26.8 mmol) from Example 46 was subjected to hydrogenation (balloon) on 10% Pd/C (2.0 g) 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 (4.31 g, 45%) 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-0ce88ca9c91e4846addcad442105f909
Source dataset
uspto-grants-2012_05
Patent number
US08178551B2

Reaction notes

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