(Dimethyl sulfide)trihydroboron → HCID 67692931, compound

HRID 1741589Notes

Reaction equation

HRID 1741589 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH:7]1[S:12](=[O:14])(=[O:13])[C:11]2[S:15][C:16]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:17][C:10]=2[CH:9]([NH:22][C:23](=O)[CH2:24][CH3:25])[CH2:8]1.CSC.B>C1COCC1>[CH3:1][O:2][CH2:3][CH2:4][O:5][CH2:6][CH:7]1[S:12](=[O:13])(=[O:14])[C:11]2[S:15][C:16]([S:18]([NH2:21])(=[O:19])=[O:20])=[CH:17][C:10]=2[CH:9]([NH:22][CH2:23][CH2:24][CH3:25])[CH2:8]1

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 67848941HCID 67848941, compound

Product 1

HCID 67692931HCID 67692931, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 11 (39.9 g, 0.021 mol) in THF (400 ml) under N2 was added dropwise 10M borane dimethylsulfide (42.5 ml, 0.42 mol). After addition, the reaction which was fitted with a short-path distillation head was heated to 60° C. for 3 h while collecting distilled dimethylsulfide and THF. The solution was then concentrated to dryness and then 6N HCl was carefully added dropwise. After addition the reaction was heated at reflux for 1/2 h, the solution was concentrated, flushed with EtOH (2×) and the residue was then carefully treated with saturated NaHCO3. The aqueous layer was extracted with EtOAc (4×) and the organic extracts were dried, filtered and concentrated to dryness. The residue was chromatographed on a Still column (120 mm) packed with silica gel and eluted with 20:1 CHCl3 --CH3OH to yield 15.4 g (40%) of trans -12 and then 4.7 g (12%) of cis-13.

Workup

  1. additionAfter addition
  2. customthe reaction which
  3. customwas fitted with a short-path distillation head
  4. customwhile collecting
  5. distillationdistilled dimethylsulfide and THF
  6. concentrationThe solution was then concentrated to dryness
  7. addition6N HCl was carefully added dropwise
  8. additionAfter addition the reaction
  9. temperaturewas heated
  10. temperatureat reflux for 1/2 h
  11. concentrationthe solution was concentrated
  12. customflushed with EtOH (2×)
  13. additionthe residue was then carefully treated with saturated NaHCO3
  14. extractionThe aqueous layer was extracted with EtOAc (4×)
  15. customthe organic extracts were dried
  16. filtrationfiltered
  17. concentrationconcentrated to dryness
  18. customThe residue was chromatographed on a Still column (120 mm)
  19. washeluted with 20:1 CHCl3
  20. customCH3OH to yield 15.4 g (40%) of trans -12

Sources & evidence

ORD record
ord-acb85114e22f4490907eb8df28ec0f4b
Source dataset
uspto-grants-1994_08
Patent number
US05334591

Reaction notes

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