Sodium borohydride → HCID 58081127, compound

HRID 2361751Notes

Reaction equation

HRID 2361751 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][C:16](=[O:19])[CH2:15][CH2:14]1)[CH:8]=[CH:7]2>CO>[Br:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH:13]1[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]1)[CH:8]=[CH:7]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 54201797HCID 54201797, compound

Product 1

HCID 58081127HCID 58081127, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

Sodium borohydride (62.198 mg, 1.644 mmol) was added to a mixture of intermediate D30 (2.074 g, 7.098 mmol) in MeOH (50 ml) stirred at 0° C. The resulting reaction mixture was warmed to room temperature and further stirred for 1 h. Subsequently, the mixture was concentrated in vacuo and the residue was dissolved in DCM. This solution was washed with NH4Cl (aqueous sat. solution). The organic layer was separated, dried (Na2SO4), and the solvent was evaporated in vacuo. The residue was purified by column chromatography (silica gel; EtOAc/heptane gradient from 0:100 to 30:70 as eluent). The desired fractions were collected and the solvent was evaporated in vacuo to yield trans-D31 (1.809 g, 86.6%) and cis-D31 (0.110 g, 5.27%).

Workup

  1. customThe resulting reaction mixture
  2. temperaturewas warmed to room temperature
  3. stirringfurther stirred for 1 h
  4. concentrationSubsequently, the mixture was concentrated in vacuo
  5. dissolutionthe residue was dissolved in DCM
  6. washThis solution was washed with NH4Cl (aqueous sat. solution)
  7. customThe organic layer was separated
  8. dry with materialdried (Na2SO4)
  9. customthe solvent was evaporated in vacuo
  10. customThe residue was purified by column chromatography (silica gel; EtOAc/heptane gradient from 0:100 to 30:70 as eluent)
  11. customThe desired fractions were collected
  12. customthe solvent was evaporated in vacuo
  13. customto yield trans-D31 (1.809 g, 86.6%) and cis-D31 (0.110 g, 5.27%)

Sources & evidence

ORD record
ord-7d880f316ebe42e9b841b3eeea44c019
Source dataset
uspto-grants-2014_04
Patent number
US08691813B2

Reaction notes

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