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

HRID 324467Notes

Reaction equation

HRID 324467 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[CH:11]=[CH:10][C:9]3[CH:12]=[C:13]([CH2:16][CH2:17][CH3:18])[CH:14]=[CH:15][C:8]=3[C:7](=[O:19])[C:5]=2[N:6]=1.[BH4-].[Na+]>CS(C)=O.O1CCOCC1>[CH3:1][C:2]1[S:3][C:4]2[CH:11]=[CH:10][C:9]3[CH:12]=[C:13]([CH2:16][CH2:17][CH3:18])[CH:14]=[CH:15][C:8]=3[CH:7]([OH:19])[C:5]=2[N:6]=1

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 220035872-Methyl-7-n-propyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-one

Product 1

HCID 70112533(+/-)-2-Methyl-7-n-propyl-4H-benzo[5,6]cyclohepta[1,2-d]thiazol-4-ol

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product from step (x) (3.1 g) in dry dimethylsulphoxide (30 ml) and dry 1,4-dioxane (90 ml) was added sodium borohydride (0.7 g). After stirring at room temperature for 24 h the reaction mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with saturated sodium bicarbonate solution, then brine. The organic layer was collected and dried over magnesium sulphate and solvent removed under reduced pressure to leave a pale yellow gum.

Workup

  1. customwas quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated sodium bicarbonate solution
  4. customThe organic layer was collected
  5. dry with materialdried over magnesium sulphate and solvent
  6. customremoved under reduced pressure
  7. customto leave a pale yellow gum

Sources & evidence

ORD record
ord-b83f1e74fee649fd994560b1902c253e
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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