Sodium borohydride → HCID 86649115, compound

HRID 1471025Notes

Reaction equation

HRID 1471025 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:22])[CH2:9][CH2:10][C:11]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:12])=[CH:4][C:3]=1[N+:23]([O-:25])=[O:24].[BH4-].[Na+]>CCO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:22])[CH2:9][CH2:10][CH:11]([C:13]2[CH:14]=[CH:15][C:16]([N+:19]([O-:21])=[O:20])=[CH:17][CH:18]=2)[OH:12])=[CH:4][C:3]=1[N+:23]([O-:25])=[O:24]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86649114HCID 86649114, compound

Product 1

HCID 86649115HCID 86649115, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the product from Example 179A (10.0 g, 27.6 mmol) in EtOH (220 mL) was added sodium borohydride (2.190 g, 57.9 mmol) in several portions over 1 h. The resulting mixture was stirred at rt for 1 h, filtered through celite, and concentrated in vacuo. The residue was dissolved in EtOAc and washed by 1N aq. HCl. The organic layer was dried over Na2SO4, filtered and concentrated in vacuo to give the title compound (9.29 g, 92%)

Workup

  1. filtrationfiltered through celite
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in EtOAc
  4. washwashed by 1N aq. HCl
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2792c3a53ae747b0ab40808860d607b9
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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