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

HRID 635871Notes

Reaction equation

HRID 635871 reaction equation
[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

Participants

4

Reactant 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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6aea519e716a4bc4a7d69bd2c40daf08
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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