Sulfuric Acid → (-)-Noroxymorphone

HRID 2115181Notes

Reaction equation

HRID 2115181 reaction equation
C(OC([N:6]1[CH2:24][CH2:23][C@:13]23[C:14]4[C:15]5[O:22][C@H:12]2[C:11](=[O:25])[CH2:10][CH2:9][C@@:8]3([OH:26])[C@H:7]1[CH2:20][C:19]=4[CH:18]=[CH:17][C:16]=5[OH:21])=O)C.S(=O)(=O)(O)O>O>[O:22]1[C@@H:12]2[C@@:13]34[CH2:23][CH2:24][NH:6][C@@H:7]([C@:8]3([OH:26])[CH2:9][CH2:10][C:11]2=[O:25])[CH2:20][C:19]2=[C:14]4[C:15]1=[C:16]([OH:21])[CH:17]=[CH:18]2

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 86596553Carbamat Noroxymorphone

Product 1

HCID 5497189(-)-NoroxymorphoneYield 122.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Product (5) (4,7 g) was dissolved in 28 ml of water and 5,6 ml of sulfuric acid and refluxed for approx. 24 h. The product was precipitated at pH=9 by dilution with water and 4,6 g of crude product (6) was obtained after filtration and drying. The product was purified by dissolution in ethanol, precipitation from this solvent at pH=2, dissolution in water, charcoal treatment and precipitation at pH=9. 1H NMR (400 M z, DMSO-d6) δ 1.17 (m, 1H), 1.41 (m, 1H), 1.72 (m, 1H), 2.07 (m, 1H), 2.29 (m, 1H), 2.36 (m, 1H), 2.62 (in 1H), 3.9 (m, 4H), 6.52 (d, 1H), 6.56 (d, 1H).

Workup

  1. customThe product was precipitated at pH=9 by dilution with water

Sources & evidence

ORD record
ord-d9ff3e9a74e149568197f2dd2a5a0202
Source dataset
uspto-grants-2008_10
Patent number
US07435817B2

Reaction notes

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