Sodium borohydride → HCID 86680443, compound

HRID 240431Notes

Reaction equation

HRID 240431 reaction equation
[O:1]=[C:2]1[CH:6]2[CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][N:5]2[CH2:4][CH2:3]1.[BH4-].[Na+]>CO>[OH:1][C@H:2]1[C@@H:6]2[CH2:7][N:8]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH2:9][CH2:10][N:5]2[CH2:4][CH2:3]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 83670762HCID 83670762, compound

Product 1

HCID 86680443HCID 86680443, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of Example 35C (46 g, 0.192 mol) in methanol (460 mL) was added NaBH4 (13 g, 0.345 mol) at approximately 0° C., and the mixture was stirred at ambient temperature for 1 hour. The reaction mixture was quenched with saturated ammonium chloride solution (100 mL), and the volatiles were removed under reduced pressure. The residue obtained was partitioned between ethyl acetate (500 mL) and water (250 mL). The organic layer was separated, dried over Na2SO4, filtered and concentrated. The material obtained was purified by column chromatography over silica gel using 5-6% methanol in chloroform to get the first eluting product (Example 36A, 5.3 g) and second eluting product (Example 35D, 5.1 g) together with 20 g of a mixture of both diastereomers.

Workup

  1. customThe reaction mixture was quenched with saturated ammonium chloride solution (100 mL)
  2. customthe volatiles were removed under reduced pressure
  3. customThe residue obtained
  4. customwas partitioned between ethyl acetate (500 mL) and water (250 mL)
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe material obtained
  10. customwas purified by column chromatography over silica gel using 5-6% methanol in chloroform

Sources & evidence

ORD record
ord-28ca3c6889b34ce58ecee7453f143f32
Source dataset
uspto-grants-2014_02
Patent number
US08648074B2

Reaction notes

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