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

HRID 324463ノート

反応式

HRID 324463 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 312751,4-Dioxane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f651970c04f04783b2c143de1cd9fe8b
出典データセット
uspto-grants-2001_04
特許番号
US06218376B1

反応ノート

読み込み中…