Ethanol → HCID 46907403, compound

HRID 2217156Notes

Reaction equation

HRID 2217156 reaction equation
[BH4-].[BH4-].[BH4-].[BH4-].[Na+].[Na+].[Na+].[Na+].[CH:9]1[C:18]2[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:12]=[CH:11][C:10]=1[C:19]1[CH2:20][CH:21]2[N:27]([CH:28]=1)[C:26](=[O:29])[C:25]1[CH:30]=[C:31]([O:36][CH3:37])[C:32]([O:34][CH3:35])=[CH:33][C:24]=1[N:23](COCC[Si](C)(C)C)[CH2:22]2.C(O)C.C1COCC1>O>[CH3:37][O:36][C:31]1[C:32]([O:34][CH3:35])=[CH:33][C:24]2[N:23]=[CH:22][C@@H:21]3[CH2:20][C:19]([C:10]4[CH:11]=[CH:12][C:13]5[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=5)[CH:9]=4)=[CH:28][N:27]3[C:26](=[O:29])[C:25]=2[CH:30]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8028TetrahydrofuranHCID 69255012HCID 69255012, compoundHCID 131720822Sodium tetraborohydride

Product 1

HCID 46907403HCID 46907403, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Solid sodium tetraborohydride (654 mg, 17.2 mmol) was added in three portions at two hourly intervals to a stirred solution of 10 (971 mg, 1.8 mmol) in a mixture of anhydrous ethanol (19 mL) and anhydrous THF (37 mL) and left to stir at room temperature for 24 hours. The reaction mixture was diluted with water (50 mL) and extracted with ethyl acetate (3×50 mL). The organic layers were evaporated in vacuo. The crude product was treated with ethanol (50 mL), water (30 mL) and silica gel (18.3 g) and left to stir at room temperature for 24 hours. The reaction mixture was filtered and the product extracted with ethyl acetate (3×50 ). The organic layers were combined and washed with brine (20 mL) and dried over anhydrous magnesium sulphate. Filtration and evaporation in vacuo afforded the crude product, which was purified using flash column chromatography with a 70-50% hexane in ethyl acetate as eluent. Pure fractions were combined and evaporated in vacuo to afford the pure product 11 as a yellow powder (151 mg, 0.39 mmol, 22% yield).

Workup

  1. waitleft
  2. extractionextracted with ethyl acetate (3×50 mL)
  3. customThe organic layers were evaporated in vacuo
  4. additionThe crude product was treated with ethanol (50 mL), water (30 mL) and silica gel (18.3 g)
  5. waitleft
  6. stirringto stir at room temperature for 24 hours
  7. filtrationThe reaction mixture was filtered
  8. extractionthe product extracted with ethyl acetate (3×50 )
  9. washwashed with brine (20 mL)
  10. dry with materialdried over anhydrous magnesium sulphate
  11. filtrationFiltration and evaporation in vacuo
  12. customafforded the crude product, which
  13. customwas purified
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-cb6d86b940fc416398bac16c6f009c35
Source dataset
uspto-grants-2008_08
Patent number
US07407951B2

Reaction notes

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