Sodium Hydroxide → HCID 15045342, compound

HRID 1645844Notes

Reaction equation

HRID 1645844 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:17][C:18]([N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]2[C:26](OC)=[O:27])=O)[CH:12]=[CH:13][C:14]=1[O:15][CH3:16].[OH-].[Na+].S([O-])([O-])(=O)=O.[Mg+2]>O1CCCC1.O.C(OCC)(=O)C>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([CH2:17][CH2:18][N:20]2[CH2:25][CH2:24][CH2:23][CH2:22][CH:21]2[CH2:26][OH:27])[CH:12]=[CH:13][C:14]=1[O:15][CH3:16]

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 15045341HCID 15045341, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 15045342HCID 15045342, compoundYield 81%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

2.33 g of lithium aluminum hydride was suspended into 50 ml of tetrahydrofuran and stirred. 3.94 g of methyl N-(3,4-dimethoxyphenylacetyl)piperidine-2-carboxylate was dissolved in 20 ml of tetrahydrofuran, which was dropped and, thereafter, refluxed for 30 min. After cooling with ice and decomposing the excess reagent with ethyl acetate, 2.3 ml of water, 2.3 ml of an aqueous 15% solution of sodium hydroxide and 7 ml of water were added successively and, further, anhydrous magnesium sulfate was added and stirred. Insoluble matters were filtered out and the filtrate was washed thoroughly with tetrahydrofuran. The filtrate was concentrated and purified on silica gel column chromatography (solvent: dichloromethane:methanol:concentrated aqueous ammonium=1000:100:2), to obtain 2.77 g of the above-captioned compound as white solid (yield: 81%).

Workup

  1. additionwhich was dropped
  2. temperaturerefluxed for 30 min
  3. temperatureAfter cooling with ice
  4. additionwere added successively
  5. stirringstirred
  6. filtrationInsoluble matters were filtered out
  7. washthe filtrate was washed thoroughly with tetrahydrofuran
  8. concentrationThe filtrate was concentrated
  9. custompurified on silica gel column chromatography (solvent: dichloromethane:methanol:concentrated aqueous ammonium=1000:100:2)

Sources & evidence

ORD record
ord-829ccf49184f4d58a3326ab8b6ad6c68
Source dataset
uspto-grants-1993_01
Patent number
US05177089

Reaction notes

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