(Dimethyl sulfide)trihydroboron → HCID 13911613, compound

HRID 653458Notes

Reaction equation

HRID 653458 reaction equation
[CH2:1]([N:3]([CH:7]1[CH2:12][CH2:11][S:10](=[O:14])(=[O:13])[C:9]2[S:15][C:16]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:17][C:8]1=2)[C:4](=O)[CH3:5])[CH3:2].CSC.B>C1COCC1>[CH2:1]([N:3]([CH:7]1[CH2:12][CH2:11][S:10](=[O:13])(=[O:14])[C:9]2[S:15][C:16]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:17][C:8]1=2)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 12423031(Dimethyl sulfide)trihydroboronHCID 14537339HCID 14537339, compound

Product 1

HCID 13911613HCID 13911613, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of product from Step A (1.8 g, 0.005 mol) in THF (40 ml) heated at reflux under N2 was added dropwise borane dimethylsulfide (10M, 1.5 ml, 0.015 mol) with the continuous removal of dimethylsulfide by way of a short path distillation apparatus. After 1 hour, the mixture was concentrated to dryness and the residue treated carefully with 6N HCl (12 ml). After heating at reflux for 0.5 hour, the mixture was concentrated to dryness. The residue was treated with NaHCO3 and the suspension extracted with ethyl acetate (4x). The organic extracts were dried, filtered and concentrated to dryness. The residue was chromatographed on silica gel and the product eluted with 5% CH3OH--CHCl3 saturated with NH3 gas. The product was crystallized as the hydrochloride salt from ethanol to yield 1.1 g of product (56%), m.p. 236°-238° C.

Workup

  1. temperatureheated
  2. temperatureat reflux under N2
  3. customwith the continuous removal of dimethylsulfide
  4. distillationby way of a short path distillation apparatus
  5. concentrationthe mixture was concentrated to dryness
  6. additionthe residue treated carefully with 6N HCl (12 ml)
  7. temperatureAfter heating
  8. temperatureat reflux for 0.5 hour
  9. concentrationthe mixture was concentrated to dryness
  10. additionThe residue was treated with NaHCO3
  11. extractionthe suspension extracted with ethyl acetate (4x)
  12. customThe organic extracts were dried
  13. filtrationfiltered
  14. concentrationconcentrated to dryness
  15. customThe residue was chromatographed on silica gel
  16. washthe product eluted with 5% CH3OH
  17. customThe product was crystallized as the hydrochloride salt from ethanol

Sources & evidence

ORD record
ord-26986cdce2f24698ab89f0105ceb96b1
Source dataset
uspto-grants-1987_06
Patent number
US04677115

Reaction notes

Loading…