Hydrochloric Acid → (-)-4,4-Diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide

HRID 375475Notes

Reaction equation

HRID 375475 reaction equation
[C:1]1([C:7]2([C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:15]3[CH:11]([CH2:12][N:13](C(OCCCCC(OC(C)(C)C)=O)=O)[CH2:14]3)[S:10](=[O:30])[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl.O1CCOCC1>ClCCl>[C:31]1([C:7]2([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[CH:15]3[CH:11]([CH2:12][NH:13][CH2:14]3)[S:10](=[O:30])[CH2:9][CH2:8]2)[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 545509644,4-Diphenyl-6-tert-butyloxycarbonylbutyloxycarbonylperhydrothiopyrano[2,3-c]pyrrole 1-oxide

Product 1

HCID 18995289(-)-4,4-Diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxideYield 123.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3.98 g of 4,4-diphenyl-6-tert-butyloxycarbonylbutyloxycarbonylperhydrothiopyrano[2,3-c]pyrrole 1-oxide (mixture of the 1RS,4aSR,7aSR and 1RS,4aRS,7aRS isomers) are treated with 40 cm3 of a mixture of concentrated hydrochloric acid (37% hydrochloric acid) and dioxane (1/2 by volume) for 48 hours at 20° C. The solution is concentrated to dryness at 40° C. under reduced pressure (2.7 kPa). The oil obtained is taken up in 30 cm3 of dichloromethane, the solution is washed with 60 cm3 of a 2N aqueous solution of sodium hydroxide, the aqueous phase is extracted with 20 cm3 of dichloromethane. The organic extracts are pooled, dried over magnesium sulphate and concentrated to dryness at 40° C. under reduced pressure (2.7 kPa). The residue is taken up in diisopropyl oxide and then concentrated to dryness at 40° C. under reduced pressure (2.7 and then 0.13 kPa). 3.0 g of (1RS,4aRS,7aRS)-4,4-diphenylperhydrothiopyrano[2,3-c]pyrrole 1-oxide are obtained in the form of a white meringue.

Workup

  1. concentrationThe solution is concentrated to dryness at 40° C. under reduced pressure (2.7 kPa)
  2. customThe oil obtained
  3. washthe solution is washed with 60 cm3 of a 2N aqueous solution of sodium hydroxide
  4. extractionthe aqueous phase is extracted with 20 cm3 of dichloromethane
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated to dryness at 40° C. under reduced pressure (2.7 kPa)
  7. concentrationconcentrated to dryness at 40° C. under reduced pressure (2.7

Sources & evidence

ORD record
ord-be1e7f3c576246459fdf23b53c10d463
Source dataset
uspto-grants-1996_01
Patent number
US05484942

Reaction notes

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