Acetic Acid → HCID 15385698, compound

HRID 1858358Notes

Reaction equation

HRID 1858358 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[CH2:10][CH2:11][C@@H:12]2[O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=2)[CH2:7][C:6]2=[C:15]4[C:2]1=[CH:3][CH:4]=[C:5]2OCOC.O.[C:32]([OH:35])(=[O:34])[CH3:33]>>[C:32]([O:35][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][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[CH2:11][CH2:10][C@@H:9]35)(=[O:34])[CH3:33]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 131722160HCID 131722160, compound

Product 1

HCID 15385698HCID 15385698, compound

Conditions

Temperature
100 °C

Procedure

4,5α-Epoxy-methoxymethoxy-17-methyl-6α-((2-pyridyl)-oxy)-morphinane (0.940 g, 2.3 mmol) is mixed with H2O (35 ml) and glacial acetic acid (35 ml) and stirred for 6 hours at 100° C. The mixture is then evaporated down at 40° C. using the Rotavapor and the residue obtained is purified by flash chromatography (90 g silica gel; CH2Cl2 /MeOH=4/1). The product is dissolved in H2O (7 ml) and glacial acetic acid (0.7 ml) and lyophilised.

Workup

  1. customThe mixture is then evaporated down at 40° C.
  2. customthe residue obtained
  3. customis purified by flash chromatography (90 g silica gel; CH2Cl2 /MeOH=4/1)
  4. dissolutionThe product is dissolved in H2O (7 ml)

Sources & evidence

ORD record
ord-968dfd5e64984989b943c7b60788ec90
Source dataset
uspto-grants-2000_11
Patent number
US06150524

Reaction notes

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