Hydrogen Bromide → HCID 67594446, compound

HRID 1419009Notes

Reaction equation

HRID 1419009 reaction equation
Cl.[O:2]1[C@:14]2([CH3:20])[C@@:15]34[CH2:17][CH2:18][NH:19][C@@H:9]([C@:10]3([O:22][CH3:23])[CH2:11][CH2:12][C:13]2=[O:21])[CH2:8][C:7]2=[C:16]4[C:3]1=[C:4]([O:24]C)[CH:5]=[CH:6]2.[BrH:26]>>[BrH:26].[O:2]1[C@:14]2([CH3:20])[C@@:15]34[CH2:17][CH2:18][NH:19][C@@H:9]([C@:10]3([O:22][CH3:23])[CH2:11][CH2:12][C:13]2=[O:21])[CH2:8][C:7]2=[C:16]4[C:3]1=[C:4]([OH:24])[CH:5]=[CH:6]2

Participants

3

Reactant 2

HCID 260Hydrogen BromideHCID 69035111HCID 69035111, compound

Product 1

HCID 67594446HCID 67594446, compoundYield 66%

Procedure

A solution of 4,5α-epoxy-3,14-dimethoxy-5-methylmorphinan-6-one hydrochloride (H. Schlnidhammer et al., Helv. Chim. Acta Vol. 77: 1585-1589, 1994) (1.0 g, 2.73 mmol) in 3.5 ml of 48% HBr was refluxed for 15 min. After cooling, the now brown solution was evaporated, the residue treated with MeOH and again evaporated (this operation was repeated once). The oily residue was crystallized from MeOH to yield 713 mg (66%) of colorless 4,5a-epoxy-3-hydroxy-14-methoxy-5-methylmorphinan-6-one hydrobromide (compound 6). M.p.>230° C. (dec.). IR (KBr): 3545 and 3495 (+NH, OH), 1720 (CO)cm-1. CI-MS:m/z 316(M+ +1). 1H-NMR(DMSO-d6):δ9.37 (s, OH), 8.65 (broad s, +NH2), 6.64 (dd, J=8.2, 8.2 Hz, 2 arom. H), 3.36 (s, OCH3 --C(14)), 1.48 (s, CH3 --C(5)). Analysis calculated for C18H21NO4. HBr. MeOH(428.33):C 53.28, H 6.12, N 3.27; found: C 53.12, H 5.97, N 3.32.

Workup

  1. temperatureAfter cooling
  2. customthe now brown solution was evaporated
  3. additionthe residue treated with MeOH
  4. customagain evaporated (this operation
  5. customThe oily residue was crystallized from MeOH

Sources & evidence

ORD record
ord-fd5421cbab294065a7faa05676225e5e
Source dataset
uspto-grants-1999_03
Patent number
US05886001

Reaction notes

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