Water → HCID 23001236, compound

HRID 397812Notes

Reaction equation

HRID 397812 reaction equation
C[O:2][C:3]([CH:5]1[C:14]2[N:13]=[CH:12][N:11]([C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:10]=2[CH2:9][CH2:8][CH2:7][CH2:6]1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[C:28]1([C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=2)[N:11]2[C:10]3[CH2:9][CH2:8][CH2:7][CH2:6][CH:5]([CH2:3][OH:2])[C:14]=3[N:13]=[CH:12]2)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59086017HCID 59086017, compound

Product 1

HCID 23001236HCID 23001236, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of 1-triphenylmethyl-1,4,5,6,7,8-hexahydrocycloheptaimidazole-4-carboxylic acid methyl ester (5.5 g, 12.6 mmol) in THF (140 ml) was added lithium aluminum hydride (9.5 ml, 1 mol/L in THF, 9.5 mmol). The mixture was stirred at 20° C. for 2 hours, and water (1.4 ml) and NaOH (1.4 ml, 4 mol/l in water) were carefully added. After stirring at room temperature for 0.5 hours, water (5 ml) was added, and after stirring for 0.5 hours the mixture was dried by addition of magnesium sulfate. Filtration, concentration, and precipitation from methanol yielded 4.4 g (86%) of the title alcohol as a solid.

Workup

  1. stirringAfter stirring at room temperature for 0.5 hours
  2. stirringafter stirring for 0.5 hours the mixture
  3. dry with materialwas dried by addition of magnesium sulfate
  4. filtrationFiltration, concentration, and precipitation from methanol

Sources & evidence

ORD record
ord-23f9440e1d4f497e860e475c06d6dba6
Source dataset
uspto-grants-2003_08
Patent number
US06610721B2

Reaction notes

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