Acetic Acid → HCID 15385702, compound

HRID 1858344Notes

Reaction equation

HRID 1858344 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][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=2)[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:32][CH2:33][O:34]C)[CH:4]=[CH:5]2.O.[C:37](O)(=O)C>>[C:33]([O:32][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][C:22]1[CH:27]=[CH:26][C:25]([C:28]([O:30][CH3:31])=[O:29])=[CH:24][CH:23]=1)[CH2:11][CH2:10][C@@H:9]35)(=[O:34])[CH3:37]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 962WaterHCID 15385701HCID 15385701, compound

Product 1

HCID 15385702HCID 15385702, compound

Conditions

Temperature
100 °C

Procedure

4,5α-Epoxy-3-methoxymethoxy-17-methyl-6α-((4-(methyloxycarbonyl)-phenyl)-methoxy)-morphinane (1.40 g, 2.92 mmol) is dissolved with water (35 ml) and glacial acetic acid (35 ml) and then stirred for 4 hours at 100° C. The volatile components are eliminated using the Rotavapor. The residue thus obtained is purified by flash chromatography (100 g of silica gel; mobile phase: methylene chloride/methanol= 4:1). The product is dissolved in a mixture of water and glacial acetic acid and lyophilised. Yield: 1.225 g 4,5α-epoxy-17-methyl-6α-((4-(methyloxycarbonyl)-phenyl)-methoxy)-morphinan-3-ol acetate (84.7%).

Workup

  1. customThe residue thus obtained
  2. customis purified by flash chromatography (100 g of silica gel; mobile phase: methylene chloride/methanol= 4:1)
  3. dissolutionThe product is dissolved in a mixture of water and glacial acetic acid

Sources & evidence

ORD record
ord-9256bb55ee1242e2a15c79d8e5e09e6c
Source dataset
uspto-grants-2000_11
Patent number
US06150524

Reaction notes

Loading…