Hydrogen Bromide → HCID 70586473, compound

HRID 904210Notes

Reaction equation

HRID 904210 reaction equation
[ClH:1].[CH:2]1([CH2:6][N:7]2[CH2:25][CH2:24][C@@:14]34[C:15]5[CH:16]=[C:17]([O:22]C)[CH:18]=[CH:19][C:20]=5[CH2:21][C@@H:8]2[C@@H:9]3[C@@H:10]([CH3:27])[CH2:11][C:12](=[O:26])[CH2:13]4)[CH2:5][CH2:4][CH2:3]1.Br.[NH4+].[OH-]>O>[ClH:1].[CH:2]1([CH2:6][N:7]2[CH2:25][CH2:24][C@@:14]34[C:15]5[CH:16]=[C:17]([OH:22])[CH:18]=[CH:19][C:20]=5[CH2:21][C@@H:8]2[C@@H:9]3[C@@H:10]([CH3:27])[CH2:11][C:12](=[O:26])[CH2:13]4)[CH2:5][CH2:4][CH2:3]1

Participants

5

Reactant 3

HCID 260Hydrogen BromideHCID 14923Ammonium HydroxideHCID 70586749HCID 70586749, compound

Product 1

HCID 70586473HCID 70586473, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A sample of 17-cyclobutylmethyl-3-methoxy-8β-methylmorphinan-6-one (prepared in Example 2) and 48% aqueous HBr (1.0 g/5 ml, respectively) was refluxed for 20 minutes in a pre-heated oil bath at 140° C. The mixture was cooled in ice and diluted with 30 ml of water. The aqueous solution was adjusted to about pH 11 by addition of concentrated NH4OH. The basic mixture was extracted with three portions of chloroform, and the organic extract was treated as in Example 1D. The residue was chromatographed over Silica Gel G as in Example 1D and the product was isolated as in the HCl salt, yield 84%, mp 150° C. dec, with foaming. The tartaric acid salt of 17-cyclobutylmethyl-3-hydroxy-8β-methylmorphinan-6-one can be prepared by procedures apparent to those skilled in the art.

Workup

  1. temperatureThe mixture was cooled in ice
  2. extractionThe basic mixture was extracted with three portions of chloroform
  3. extractionthe organic extract
  4. additionwas treated as in Example 1D
  5. customThe residue was chromatographed over Silica Gel G as in Example 1D

Sources & evidence

ORD record
ord-b26b0a9c601846789f8345d79fb1aab6
Source dataset
uspto-grants-1980_10
Patent number
US04230712

Reaction notes

Loading…