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1-Methylpyrrolidine → Triphenylsulfonium 1-((3-methacryloyloxyadamantyl)methoxycarbonyl)difluoromethansulfonate

HRID 389000
Notes
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Reaction equation

HRID 389000 reaction equation
[OH:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([CH2:12][O:13][C:14]([C:16]([F:22])([F:21])[S:17]([O-:20])(=[O:19])=[O:18])=[O:15])([CH2:5]3)[CH2:3]1)[CH2:9]2.[C:23]1([S+:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1.CN1CCCC1.[CH3:48][C:49]([C:51](Cl)=[O:52])=[CH2:50].COC(C)(C)C>C(Cl)(Cl)Cl>[C:51]([O:1][C:2]12[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:10][C:4]([CH2:12][O:13][C:14]([C:16]([F:22])([F:21])[S:17]([O-:20])(=[O:18])=[O:19])=[O:15])([CH2:5]3)[CH2:3]1)[CH2:9]2)(=[O:52])[C:49]([CH3:50])=[CH2:48].[C:36]1([S+:29]([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 84541-Methylpyrrolidine2×HCID 13528Methacryloyl chloride2×HCID 15413tert-Butyl methyl etherHCID 75607088Triphenylsulfonium (3-hydroxytricyclo[3.3.1.13,7]decane-1-methoxycarbonyl)difluoromethane sulfonate

Product 1

HCID 86613394Triphenylsulfonium 1-((3-methacryloyloxyadamantyl)methoxycarbonyl)difluoromethansulfonate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent4×

Procedure

2.8 parts of triphenylsulfonium 1-((3-hydroxyadamantyl)methoxycarbonyl)difluoromethanesulfonate and 1.0 part of 1-methylpyrrolidine were dissolved in 30 parts of chloroform. A solution of 0.7 Part of methacryl chloride and 2.2 parts of chloroform was added dropwise to the solution at room temperature and then the resultant mixture was stirred at room temperature for about 3 days and at 40° C. for 7.5 hours. After cooling to room temperature, 1.0 part of 1-methylpyrrolidine was added to the reaction mixture and a solution of 0.7 part of methacryl chloride and 2.2 parts of chloroform was added thereto at room temperature. After reacting at room temperature for 14 hours, the reaction mixture was diluted with 30 parts of chloroform and quenched with 36 parts of ion-exchanged water in an ice bath. A chloroform layer was separated and repeatedly washed with ion-exchanged water. To the chloroform layer, 1.1 parts of active carbon was added and the mixture was stirred for 1 hour. The mixture was filtered and chloroform layer obtained was concentrated to obtain pale yellow oily matters. To the oily matters, tert-butyl methyl ether was added to stir and the mixture was filtered to obtain 2.8 parts of triphenylsulfonium 1-((3-methacryloyloxyadamantyl)methoxycarbonyl)difluoromethansulfonate in the form of white solid, which is called as TPS-4.

Workup

  1. customat room temperature
  2. customquenched with 36 parts of ion-exchanged water in an ice bath
  3. customA chloroform layer was separated
  4. washrepeatedly washed with ion-exchanged water
  5. additionTo the chloroform layer, 1.1 parts of active carbon was added
  6. filtrationThe mixture was filtered
  7. customchloroform layer obtained
  8. concentrationwas concentrated
  9. customto obtain pale yellow oily matters
  10. stirringto stir
  11. filtrationthe mixture was filtered

Sources & evidence

ORD record
ord-e469c1cc508c4c5f8901f3cddb6724a2
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08378016B2

Reaction notes

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