Ethylene Glycol → HCID 117857408, compound

HRID 1483149Notes

Reaction equation

[CH3:1][N:2]1[C@@H:19]2[CH2:20][C:7]3=[CH:8][CH:9]=[C:10]([OH:21])[C:11]4[O:12][C@H:13]5[C:14]([CH2:16][CH2:17][C@@H:18]2[C@:5]5([C:6]=43)[CH2:4][CH2:3]1)=[O:15].Cl.CS(O)(=O)=O.[CH2:28](O)[CH2:29][OH:30]>>[CH3:1][N:2]1[CH2:3][CH2:4][C@@:5]23[C:6]4[C:7]5[CH2:20][C@@H:19]1[C@@H:18]2[CH2:17][CH2:16][C:14]1([C@@H:13]3[O:12][C:11]=4[C:10]([OH:21])=[CH:9][CH:8]=5)[O:30][CH2:29][CH2:28][O:15]1

Participants

Reactant 3

HCID 174Ethylene Glycol

HCID 6395Methanesulfonic Acid

HCID 5462347Hydromorphone Hydrochloride

Product 1

HCID 117857408HCID 117857408, compoundYield 99.9%

Conditions

Temperature: 80 °C

Procedure

To Hydromorphone HCl (15.0 g, 46.7 mmol) was added ethylene glycol (80 mL) and methane sulfonic acid (10 mL) and the reaction heated at 80° C. overnight. The reaction was cooled to room temperature and poured into ice/NH3(aq) (˜350 mL). The product was extracted with dichloromethane and dried over MgSO4 before concentration under reduced pressure to give (4R,4aR,7aR,12bS)-3-methyl-1,2,3,4,4a,5,6,7a-octahydrospiro[4,12-methanobenzofuro[3,2-e]isoquinoline-7,2′-[1,3]dioxolan]-9-ol (19 g, 99.9% LCMS); [M+H]+ 330.5. This was taken onto the next step without purification.

Workup

temperatureThe reaction was cooled to room temperature
extractionThe product was extracted with dichloromethane
dry with materialdried over MgSO4 before concentration under reduced pressure

Sources & evidence

ORD record: ord-55877d2c5b9c439cb8e48370652ed9c8
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09416137B2

Reaction notes

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