Diethyl Ether → p-Toluenesulfonic acid

HRID 42535Notes

Reaction equation

HRID 42535 reaction equation
[C:1]1([C@H:7]([NH:9][C@@H:10]2[CH2:19][CH2:18][C:13]3([O:17][CH2:16][CH2:15][O:14]3)[CH2:12][C@@H:11]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CCOCC.O.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37]([OH:40])(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(OCC)(=O)C>[C:1]1([C@H:7]([NH:9][C@@H:10]2[CH2:19][CH2:18][C:13]3([O:17][CH2:16][CH2:15][O:14]3)[CH2:12][C@@H:11]2[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH3:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:31]1([CH3:41])[CH:32]=[CH:33][C:34]([S:37]([OH:40])(=[O:38])=[O:39])=[CH:35][CH:36]=1

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 521998p-Toluenesulfonic acid monohydrateHCID 58997721HCID 58997721, compound

Product 2

HCID 6101p-Toluenesulfonic acidYield 87.1%HCID 58997721HCID 58997721, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

(7S,8R)-Ethyl 8-((R)-1-phenylethylamino)-1,4-dioxaspiro[4.5]decane-7-carboxylate (7.80 g, 23.39 mmol) was dissolved in ethyl acetate (40 mL) at 25° C. with stirring. Et2O (40 mL) was then added followed by the addition of p-toluenesulfonic acid-monohydrate (4.45 g, 23.39 mmol) in one portion. Precipitation occurred almost immediately. The mixture was stirred for ½ hour, after which the precipitate was collected by filteration. The solids were rinsed with Et2O and then dried under high vacuum to yield (7S,8R)-ethyl 8-((R)-1-phenylethylamino)-1,4-dioxaspiro[4.5]decane-7-carboxylate, p-toluenesulfonic acid (10.3 g, 20.37 mmol, 87% yield) as an off-white solid. MS (ESI+)=334.30 (M+H)+.

Workup

  1. customPrecipitation
  2. stirringThe mixture was stirred for ½ hour
  3. customafter which the precipitate was collected by filteration
  4. washThe solids were rinsed with Et2O
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-b77d2b0f70834976b7a5bbe7fdb7a7a9
Source dataset
uspto-grants-2013_09
Patent number
US08536198B2

Reaction notes

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