Sodium Sulfate → HCID 22381732, compound

HRID 895773Notes

Reaction equation

HRID 895773 reaction equation
[CH2:1]1[C:12]2[C:11]3[C:6](=[C:7]([CH:13]=O)[CH:8]=[CH:9][CH:10]=3)[NH:5][C:4]=2[CH2:3][CH2:2]1.Cl.[NH2:16]O.[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1.N1C=CC=CC=1>[CH2:1]1[C:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[C:7]([CH2:13][NH2:16])[C:6]=3[NH:5][C:4]=2[CH2:3][CH2:2]1

Participants

7

Reactant 4

HCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochlorideHCID 21226445Aluminium lithium hydrideHCID 22381746HCID 22381746, compound

Product 1

HCID 22381732HCID 22381732, compoundYield 58.2%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 1,2,3,4-tetrahydrocyclopenta[b]indole-5-carbaldehyde (578 mg, 3.12 mmol), hydroxylamine hydrochloride (238 mg, 3.42 mmol) and pyridine (3 mL) in THF (15 mL) was stirred at rt. After 5.5 h, the reaction mixture was cooled to 0-5° C. in an ice-bath before LAH power (474 mg, 12.5 mmol) was added portionwise. The reaction mixture was then warmed to rt overnight before a sat'd Na2SO4 solution (1 mL) was added dropwise to quench the excess reagent. After 30 min of stirring, solid Na2SO4 and Et2O (30 mL) were added. The suspension was filtered and concentrated in vacuo to give 338 mg (58%) of the title compound as a yellow solid.

Workup

  1. additionwas added portionwise
  2. additionwas added dropwise
  3. customto quench the excess reagent
  4. stirringAfter 30 min of stirring
  5. additionsolid Na2SO4 and Et2O (30 mL) were added
  6. filtrationThe suspension was filtered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-90cd5539ebfd455c87a5e11b094b8e50
Source dataset
uspto-grants-2005_07
Patent number
US06916922B2

Reaction notes

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