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

HRID 635871노트

반응식

HRID 635871 반응식
[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

참가 물질

4

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-6aea519e716a4bc4a7d69bd2c40daf08
출처 데이터셋
uspto-grants-2001_02
특허 번호
US06191124B1

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