Sodium borohydride → HCID 10490611, compound

HRID 1421246Notes

Reaction equation

HRID 1421246 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:15](=[O:16])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:17]=1.[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:15]([OH:16])[C:10]3=[N:11][CH:12]=[CH:13][CH:14]=[C:9]3[CH2:8][CH2:7][C:6]=2[CH:17]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 98162608-Chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one

Product 1

HCID 10490611HCID 10490611, compoundYield 80.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 25.03 g (103 mmol) of 8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-one in 200 mL of MeOH at room temperature and under a nitrogen atmosphere was added portionwise over a period of about 1 hour 4.82 g (124 mmol) of NaBH4. Occasional cooling with an ice bath was necessary at times during the addition in order to avoid excessive reflux. After 1.6 hours the mixture was poured into ice cold water and then extracted with EtOAc (3×). The combined organic portions were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The residue was recrystallized from hot isopropyl ether. The remaining filtrate was purified via flash chromatography (20% EtOAc in hexanes) to yield more product which solidified on standing. Both batches were combined to yield 20.41 g of the title compound as a white solid.

Workup

  1. temperatureOccasional cooling with an ice bath
  2. additionwas necessary at times during the addition in order
  3. additionAfter 1.6 hours the mixture was poured into ice cold water
  4. extractionextracted with EtOAc (3×)
  5. washThe combined organic portions were washed with brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallized from hot isopropyl ether
  10. customThe remaining filtrate was purified via flash chromatography (20% EtOAc in hexanes)
  11. customto yield more product which

Sources & evidence

ORD record
ord-b7cf92fe0c82437a92bc0cb7c6bfbbee
Source dataset
uspto-grants-2000_06
Patent number
US06075025

Reaction notes

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