Hydrochloric Acid → HCID 13020700, compound

HRID 1680677Notes

Reaction equation

HRID 1680677 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:12]2=[O:20])[CH2:7][C:6]2=[C:15]4[C:2]1=[C:3]([O:21][CH3:22])[CH:4]=[CH:5]2.[OH2:23].[CH2:24]=O.Cl.[O:27]1CCOC[CH2:28]1>>[OH:27][CH2:28][C:11]1([CH2:24][OH:23])[CH2:10][C@@H:9]2[C@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]2[CH2:7][C:6]2[CH:5]=[CH:4][C:3]([O:21][CH3:22])=[C:2]([O:1][C@H:13]3[C@@H:12]1[OH:20])[C:15]4=2

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 962WaterHCID 312751,4-DioxaneHCID 5284569Hydrocodone

Product 1

HCID 13020700HCID 13020700, compoundYield 72%

Procedure

To a solution of 4,5α-epoxy-3-methoxy-17-methyl-morphinan-6-one (1a, 30.0 g, 0.10 mole) in dioxane (500 ml) was added H2O (600 ml), Ca(OH)2 (14.0 g. 0.19 mole) and 37% w/w formaldehyde solution (140 ml, 1.86 mole). The mixture was stirred at room temperature overnight and then concentrated under reduced pressure. The residue was diluted with H2O and extracted with EtOAc. Processing in the usual manner gave a white foam which was converted to the HCl salt. Crystallization from aqueous EtOH gave 28.7 g (72%) of 2a in three crops. Recyrstallization from aqueous EtOH gave pure 2a. HCl, mp>265°. Elemental analysis was consistent with this formula.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionThe residue was diluted with H2O
  3. extractionextracted with EtOAc
  4. customProcessing in the usual manner gave a white foam which
  5. customCrystallization from aqueous EtOH

Sources & evidence

ORD record
ord-2d012ca50d1e495ba6954f887123b0bc
Source dataset
uspto-grants-1981_06
Patent number
US04275205

Reaction notes

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