Sodium borohydride → (+/-)-7-Ethyl-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-ol

HRID 324463Notes

Reaction equation

HRID 324463 reaction equation
[BH4-].[Na+].Br[CH:4]([C:6]1[CH:7]=[CH:8][C:9]2[C:19](=[O:20])[C:14]3[N:15]=[C:16]([CH3:18])[S:17][C:13]=3[CH:12]=[CH:11][C:10]=2[CH:21]=1)[CH3:5]>O1CCOCC1.CS(C)=O>[CH2:4]([C:6]1[CH:7]=[CH:8][C:9]2[CH:19]([OH:20])[C:14]3[N:15]=[C:16]([CH3:18])[S:17][C:13]=3[CH:12]=[CH:11][C:10]=2[CH:21]=1)[CH3:5]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 220036097-(1-Bromoethyl)-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazole-4-one

Product 1

HCID 70113719(+/-)-7-Ethyl-2-methyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-ol

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of sodium borohydride (0.31 g) and the product from step (x) (1.35 g) in 1,4-dioxan (40 ml) and dimethyl sulphoxide (10 ml) was stirred at room temperature for 18 hours. The reaction was quenched with water (4 ml) before solvent was removed under reduced pressure. The residue was dissolved in ethyl acetate which was washed with saturated aqueous sodium bicarbonate and saturated brine. The organic phase was collected, dried (MgSO4) and evaporation of solvent under reduced pressure gave a yellow oil which was purified by chromatography, eluting with 20% isohexane in ethyl acetate.

Workup

  1. customThe reaction was quenched with water (4 ml) before solvent
  2. customwas removed under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate which
  4. washwas washed with saturated aqueous sodium bicarbonate and saturated brine
  5. customThe organic phase was collected
  6. customdried
  7. custom(MgSO4) and evaporation of solvent under reduced pressure
  8. customgave a yellow oil which
  9. customwas purified by chromatography
  10. washeluting with 20% isohexane in ethyl acetate

Sources & evidence

ORD record
ord-f651970c04f04783b2c143de1cd9fe8b
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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