Sodium borohydride → HCID 69080977, compound

HRID 2059737Notes

Reaction equation

HRID 2059737 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1/[C:11](/[C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=1)=[N:12]/[S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14].[BH4-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[CH:11]([C:19]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[N:20]=1)[NH:12][S:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 87682659HCID 87682659, compound

Product 1

HCID 69080977HCID 69080977, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

The product of Step B (2.41 g, 6.69 mmol) was dissolved in MeOH (60 mL), cooled to 0° C., and NaBH4 (0.51 g, 13.37 mmol) was added portionwise. The reaction was aged for 45 min and was quenched with saturated aq NH4Cl. The reaction was concentrated. The resulting paste was diluted in EtOAc and washed with brine. The organic portion was isolated, dried with Na2SO4, filtered and concentrated. The residue was purified by flash chromatography on silica gel gradient eluted with 0 to 100% EtOAc/hexane, affording a mixture of two diastereomers.

Workup

  1. customwas quenched with saturated aq NH4Cl
  2. concentrationThe reaction was concentrated
  3. additionThe resulting paste was diluted in EtOAc
  4. washwashed with brine
  5. customThe organic portion was isolated
  6. dry with materialdried with Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified by flash chromatography on silica gel gradient
  10. washeluted with 0 to 100% EtOAc/hexane
  11. customaffording
  12. additiona mixture of two diastereomers

Sources & evidence

ORD record
ord-dab03e129c5e4900a6011981edb57519
Source dataset
uspto-grants-2012_10
Patent number
US08278304B2

Reaction notes

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