Sodium borohydride → HCID 86714088, compound

HRID 576413Notes

Reaction equation

HRID 576413 reaction equation
[CH3:1][N:2]([CH3:26])[C:3](=[O:25])[S:4][C:5]1[C:10]([Cl:11])=[C:9]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[CH:15][CH:14]=2)[CH:8]=[C:7]([Br:21])[C:6]=1[CH2:22][CH:23]=[O:24].[BH4-].[Na+]>C1COCC1.CO>[CH3:26][N:2]([CH3:1])[C:3](=[O:25])[S:4][C:5]1[C:10]([Cl:11])=[C:9]([CH2:12][C:13]2[CH:14]=[CH:15][C:16]([O:19][CH3:20])=[CH:17][CH:18]=2)[CH:8]=[C:7]([Br:21])[C:6]=1[CH2:22][CH2:23][OH:24]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86714089HCID 86714089, compound

Product 1

HCID 86714088HCID 86714088, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of compound 219 (1.46 g, 3.18 mmol) in THF/MeOH (70 mL/7 mL) were added NaBH4 (132 mg, 3.50 mmol) at 0° C. under nitrogen atmosphere. After stirring at 0° C. for 2 hrs, the reaction mixture was quenched with saturated NaHCO4 (50 mL) and extracted with ethyl acetate (100 mL×2). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by silica gel column chromatography to provide the compound 220 (1.02 g, 2.22 mmol, 70%).

Workup

  1. customthe reaction mixture was quenched with saturated NaHCO4 (50 mL)
  2. extractionextracted with ethyl acetate (100 mL×2)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b59313e157ae442e807723d06cf97744
Source dataset
uspto-grants-2015_05
Patent number
US09034921B2

Reaction notes

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