Aluminium lithium hydride → HCID 21256484, compound

HRID 635855Notes

Reaction equation

HRID 635855 reaction equation
C([O:3][C:4]([C:6]1[N:13]2[C:9]([S:10][C:11]3[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][C:12]=32)=[N:8][CH:7]=1)=O)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[N:8]1[CH:7]=[C:6]([CH2:4][OH:3])[N:13]2[C:12]3[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][C:11]=3[S:10][C:9]=12

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 54083443HCID 54083443, compound

Product 1

HCID 21256484HCID 21256484, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 6,7,8,9-Tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazole-3-carboxylic acid ethyl ester (Formula G-4)(11.7 g) in THF (50 mL) was treated with LiAlH4 (2.24 g) at 0° and reacted at ambient temperature for 1.5 hours. The reaction was quenched by serial additions of water and 15% sodium hydroxide. The mixture was filtered and the filtrate was evaporated to yield crude 6,7,8,9-Tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazole-3-methanol (Formula G-5). Crystallization of crude 6,7,8,9-Tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazole-3-methanol (Formula G-5) from iso-propanol solution gave pure 6,7,8,9-Tetrahydro-5H-cyclohept [d]imidazo[2,1-b]thiazole-3-methanol (Formula G-5) (7.7 g) m.p. 145-146°.

Workup

  1. customreacted at ambient temperature for 1.5 hours
  2. customThe reaction was quenched by serial additions of water and 15% sodium hydroxide
  3. filtrationThe mixture was filtered
  4. customthe filtrate was evaporated
  5. customto yield crude 6,7,8,9-Tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazole-3-methanol (Formula G-5)
  6. customCrystallization of crude 6,7,8,9-Tetrahydro-5H-cyclohept[d]imidazo[2,1-b]thiazole-3-methanol (Formula G-5) from iso-propanol solution

Sources & evidence

ORD record
ord-9aef184b0f754d838d3fa680459af5bf
Source dataset
uspto-grants-2001_02
Patent number
US06191124B1

Reaction notes

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