Water → HCID 10613884, compound

HRID 260916Notes

Reaction equation

HRID 260916 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[N:7]12[CH2:14][CH2:13][CH2:12][C:11]1([CH2:15][N:16]([C:19]1[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([O:29][CH3:30])=[CH:21][CH:20]=1)C=O)[CH2:10][CH2:9][CH2:8]2.O>C1COCC1>[N:7]12[CH2:14][CH2:13][CH2:12][C:11]1([CH2:15][NH:16][C:19]1[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:22]([O:29][CH3:30])=[CH:21][CH:20]=1)[CH2:10][CH2:9][CH2:8]2

Participants

5

Reactant 3

HCID 962WaterHCID 10592080HCID 10592080, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 10613884HCID 10613884, compoundYield 65.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To lithium aluminum hydride (1.76 g, 46.3 mmol) in THF (43 ml), 1-[N-(1-Azabicyclo[3.3.0 ]octan-5-yl )methyl-N-formylamino]-4-methoxynaphthalene (3.00 g, 9.26 mmol) in THF (15 ml) was added dropwise at room temperature. After refluxed for 1 hour, the reaction mixture was cooled and chilled water was added dropwise. Formed solids were removed by filtration and the filtrate was concentrated in vacuo and purified by chromatography to afford the desired compound (1.80 g, 62.7%), as a pale yellow liquid.

Workup

  1. temperatureAfter refluxed for 1 hour
  2. temperaturethe reaction mixture was cooled
  3. additionwas added dropwise
  4. customFormed solids
  5. customwere removed by filtration
  6. concentrationthe filtrate was concentrated in vacuo
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-c18405b0fe3b4ac99e2072ab3137a001
Source dataset
uspto-grants-1996_06
Patent number
US05530138

Reaction notes

Loading…