Water → HCID 68457700, compound

HRID 254278Notes

Reaction equation

HRID 254278 reaction equation
O1[C:5]2([CH2:9][CH2:8][N:7]([C@H:10]3[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]3[O:16][CH2:17][CH2:18][C:19]3[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=3[Cl:26])[CH2:6]2)[O:4]CC1.S([O-])(=O)(=O)C.O>COCCOC>[ClH:25].[O:4]=[C:5]1[CH2:9][CH2:8][N:7]([C@H:10]2[CH2:15][CH2:14][CH2:13][CH2:12][C@@H:11]2[O:16][CH2:17][CH2:18][C:19]2[C:24]([Cl:25])=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:26])[CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 85257MethanesulfonateHCID 86608893HCID 86608893, compound

Product 1

HCID 68457700HCID 68457700, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

(1R,2R)/(1S,2S)-2-[1,4-Dioxa-7-azaspiro[4.4]non-7-yl]-1-(2,6-dichlorophenethoxy)cyclohexane: The mesylate (vi) in anhydrous ethylene glycol dimethyl ether (80 mL) was added quickly to the alkoxide mixture (viii) and the resulting mixture was readily refluxed for 66 hours. The cooled reaction mixture was poured into water (200 mL) and the organic solvent was evaporated in vacuo. The residual aqueous solution was diluted with more water to a volume of 700 mL, acidified to pH 0.5 with 6M HCl aqueous solution and extracted with diethyl ether (2×600 mL). The pH of the aqueous layer was adjusted to pH 5.9 and then the aqueous solution was extracted with diethyl ether (700 mL). The organic extract was dried over sodium sulfate and the solvent was evaporated in vacuo to yield 34.0 g of the title compound (70% yield).

Workup

  1. temperaturethe resulting mixture was readily refluxed for 66 hours
  2. customThe cooled reaction mixture
  3. customthe organic solvent was evaporated in vacuo
  4. additionThe residual aqueous solution was diluted with more water to a volume of 700 mL
  5. extractionextracted with diethyl ether (2×600 mL)
  6. extractionthe aqueous solution was extracted with diethyl ether (700 mL)
  7. extractionThe organic extract
  8. dry with materialwas dried over sodium sulfate
  9. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-3106b9da21e846578da94fe885bd47ee
Source dataset
uspto-grants-2011_01
Patent number
US07875611B2

Reaction notes

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