Sodium borohydride → HCID 58226759, compound

HRID 1470940Notes

Reaction equation

HRID 1470940 reaction equation
[Br: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][CH:3]=1.[BH4-].[Na+]>C(O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:22])[CH2:9][CH2:10][CH:11]([C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)[OH:12])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 58226578HCID 58226578, compound

Product 1

HCID 58226759HCID 58226759, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Dissolved the product from Example 39A (3.64 g, 10.05 mmol) in ethanol (67 mL) and added sodium borohydride (0.837 g, 22.11 mmol) portionwise. After stirring for 1 h at room temperature, the mixture was filtered through celite and washed with methanol and ethyl acetate and the filtrate concentrated to a solid. The solid was dissolved in ethyl acetate (200 mL) and extracted with 1N aq. HCl (200 mL), then brine and the organic layer dried and concentrated to a colorless oil (3.68 g, 100%) that was used directly in the next reaction.

Workup

  1. filtrationthe mixture was filtered through celite
  2. washwashed with methanol and ethyl acetate
  3. concentrationthe filtrate concentrated to a solid
  4. dissolutionThe solid was dissolved in ethyl acetate (200 mL)
  5. extractionextracted with 1N aq. HCl (200 mL)
  6. dry with materialbrine and the organic layer dried
  7. concentrationconcentrated to a colorless oil (3.68 g, 100%) that
  8. customwas used directly in the next reaction

Sources & evidence

ORD record
ord-98420266a831437085d57104bf9919dd
Source dataset
uspto-grants-2015_04
Patent number
US09006387B2

Reaction notes

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