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

HRID 324463노트

반응식

HRID 324463 반응식
[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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 312751,4-Dioxane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-f651970c04f04783b2c143de1cd9fe8b
출처 데이터셋
uspto-grants-2001_04
특허 번호
US06218376B1

반응 노트

불러오는 중…