Acetic Acid → HCID 20638251, compound

HRID 1858342Notes

Reaction equation

HRID 1858342 reaction equation
[O:1]1[C@@H:13]2[C@@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@@H:9]3[CH:10]=[CH:11][C@@H:12]2[O:20][CH2:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][O:23]2)[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:28][CH2:29][O:30]C)[CH:4]=[CH:5]2.[C:32](O)(=O)C>O>[C:29]([O:28][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:18]([CH3:19])[CH2:17][CH2:16][C@:14]45[C:15]=2[C:2]=1[O:1][C@H:13]4[C@@H:12]([O:20][CH2:21][CH:22]1[CH2:27][CH2:26][CH2:25][CH2:24][O:23]1)[CH:11]=[CH:10][C@@H:9]35)(=[O:30])[CH3:32]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 15840756HCID 15840756, compound

Product 1

HCID 20638251HCID 20638251, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4,5α-Epoxy-3-methoxymethoxy-17-methyl-6α-((2-tetrahydropyranyl)-methoxy)-morphinan-7-ene (2.17 g, 5.08 mmol) is dissolved in water (65 ml) and glacial acetic acid (65 ml) and then stirred for 6 hours at 100° C. The volatile components are eliminated using the Rotavapor. The residue thus obtained is purified by flash chromatography (130 g of silica gel; mobile phase: methylene chloride/methanol=9:1). The product is dissolved in a mixture of water and glacial acetic acid and lyophilised. Yield: 1.55 g 4,5α-epoxy-17-methyl-6α-((2-tetrahydropyranyl)-methoxy)-morphinan-7-en-3-ol acetate (68.8%).

Workup

  1. customThe residue thus obtained
  2. customis purified by flash chromatography (130 g of silica gel; mobile phase: methylene chloride/methanol=9:1)
  3. dissolutionThe product is dissolved in a mixture of water and glacial acetic acid

Sources & evidence

ORD record
ord-7d4034cf534046029fd8e285dd142c6c
Source dataset
uspto-grants-2000_11
Patent number
US06150524

Reaction notes

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