Sodium borohydride → HCID 178434242, compound

HRID 2307807Notes

Reaction equation

HRID 2307807 reaction equation
[C:1]([O:5][C:6](=[O:36])[NH:7][C@@H:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[C:13]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][N:23]=[C:22]3[CH3:28])[CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[BH4-].[Na+]>CCO.O>[C:1]([O:5][C:6](=[O:36])[NH:7][C@@H:8]([CH2:29][C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[C:13]([C:19]2[CH:20]=[C:21]3[C:25](=[CH:26][CH:27]=2)[NH:24][N:23]=[C:22]3[CH3:28])[CH:12]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 178434241HCID 178434241, compound

Product 1

HCID 178434242HCID 178434242, compoundYield 66.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of Example 247B (225 mg; 0.46 mmol) in EtOH (4 mL) was treated portionwise with NaBH4 (26 mg; 0.70 mmol) and stirred for 30 min., diluted with water, and extracted into EtOAc. The extracts were rinsed with brine, dried (MgSO4), concentrated, and purified by flash chromatography (60% EtOAc/hexane) to provide the desired product (150 mg; 66%).

Workup

  1. extractionextracted into EtOAc
  2. washThe extracts were rinsed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. custompurified by flash chromatography (60% EtOAc/hexane)

Sources & evidence

ORD record
ord-73fdb433e57c4eacbb02317a81762e48
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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