Diisopropyl Ether → HCID 13607943, compound

HRID 1981777Notes

Reaction equation

HRID 1981777 reaction equation
C([N:8]1[CH2:12][CH2:11][CH:10](SC2C=CC=CC=2)[CH2:9]1)C1C=CC=CC=1.Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[O:22].C(OC(C)C)(C)C.Cl[C:38]1[CH:39]=[C:40]([CH:45]=[CH:46][CH:47]=1)C(OO)=O.[S:48](=[O:51])(O)[O-:49].[Na+]>C(Cl)Cl>[C:24]1([O:23][C:21]([N:8]2[CH2:12][CH2:11][CH:10]([S:48]([C:38]3[CH:39]=[CH:40][CH:45]=[CH:46][CH:47]=3)(=[O:51])=[O:49])[CH2:9]2)=[O:22])[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 5

HCID 7914Diisopropyl EtherHCID 15891Phenyl chloroformateHCID 70297m-Chloroperbenzoic acidHCID 13607938HCID 13607938, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 13607943HCID 13607943, compoundYield 76.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 95.23 g (0.354 mole) of 1-benzyl-3-(phenylthio)pyrrolidine and 64 g (0.409 mole) of phenyl chloroformate in methylene chloride was stirred at room temperature for several hours. Excess isopropyl ether was added and the precipitate which formed was filtered off and discarded. The filtrate was dried over magnesium sulfate and the solvent was removed in vacuo. The residue was dissolved in methylene chloride and 175 g of 80% (0.814 mole) m-chloroperoxybenzoic acid was added. The solution was stirred overnight at room temperature. An aqueous solution of sodium bisulfite was added and the mixture was stirred for several hours and the phases separated. The methylene chloride phase was extracted with dilute aqueous sulfuric acid followed with dilute aqueous sodium hydroxide, the aqueous phases being discarded. The methylene chloride phase was dried over magnesium sulfate and the solvent removed in vacuo to give an oil residue. The oil crystallized from a mixture of methylene chloride and diethyl ether to give 89.26 g (76.2%) white crystals, m.p. 84°-85° C.

Workup

  1. customthe precipitate which formed
  2. filtrationwas filtered off
  3. dry with materialThe filtrate was dried over magnesium sulfate
  4. customthe solvent was removed in vacuo
  5. dissolutionThe residue was dissolved in methylene chloride
  6. stirringthe mixture was stirred for several hours
  7. customthe phases separated
  8. extractionThe methylene chloride phase was extracted with dilute aqueous sulfuric acid
  9. dry with materialThe methylene chloride phase was dried over magnesium sulfate
  10. customthe solvent removed in vacuo
  11. customto give an oil residue
  12. customThe oil crystallized from a mixture of methylene chloride and diethyl ether

Sources & evidence

ORD record
ord-208c6b17bb3340a587fabdf1c615010d
Source dataset
uspto-grants-1986_06
Patent number
US04593102

Reaction notes

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