Aluminium lithium hydride → alpha-[2-(3-fluorophenyl) ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol

HRID 635871ノート

反応式

HRID 635871 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]([C:12]2[N:19]3[C:15]([S:16][C:17]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C:18]=43)=[N:14][CH:13]=2)=[O:11])[CH:5]=[CH:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:8][CH2:9][CH:10]([C:12]2[N:19]3[C:15]([S:16][C:17]4[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][C:18]=43)=[N:14][CH:13]=2)[OH:11])[CH:5]=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 21226445Aluminium lithium hydrideHCID 700570593-(3-Fluorophenyl)-1-(6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-yl)-2-propene-1-one

生成物 1

HCID 467116alpha-[2-(3-fluorophenyl) ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A suspension of 3-(3-fluorophenyl)-1-(6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-yl)-2-propene-1-one (Formula N-6, X=3-fluoro), 1.02 g, in THF (100 mL) at −78° was treated with LiAlH4 (0.27 g) and reacted for 18 hours. The mixture was then maintained at −20° for 24 hours and excess reagent was quenched. The mixture was filtered, the filtrate was concentrated, the residue was dissolved in ethyl acetate, washed with saline, dried and evaporated. The residue (0.30 g) was crystallized from acetonitrile to yield pure α-[2-(3-fluorophenyl) ethyl]-6,7,8,9-tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazol-3-methanol, 0.21 g (m.p. 141-144°), Formula N-7, X=3-fluoro.

後処理

  1. customreacted for 18 hours
  2. temperatureThe mixture was then maintained at −20° for 24 hours
  3. customexcess reagent was quenched
  4. filtrationThe mixture was filtered
  5. concentrationthe filtrate was concentrated
  6. dissolutionthe residue was dissolved in ethyl acetate
  7. washwashed with saline
  8. customdried
  9. customevaporated
  10. customThe residue (0.30 g) was crystallized from acetonitrile

出典と根拠

ORDレコード
ord-6aea519e716a4bc4a7d69bd2c40daf08
出典データセット
uspto-grants-2001_02
特許番号
US06191124B1

反応ノート

読み込み中…