Sodium Hydroxide → HCID 11992612, compound

HRID 421819Notes

Reaction equation

HRID 421819 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][N:8]=[C:7]([N:11]2[CH2:16][CH2:15][N:14]([C:17]([O:19][CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:18])[CH2:13][CH2:12]2)[CH:6]=1)=O.[BH4-].[Li+].[OH-].[Na+]>O1CCCC1.C(OCC)(=O)C>[OH:2][CH2:3][C:5]1[CH:10]=[CH:9][N:8]=[C:7]([N:11]2[CH2:12][CH2:13][N:14]([C:17]([O:19][CH2:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:18])[CH2:15][CH2:16]2)[CH:6]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 4148881Lithium borohydrideHCID 11992422HCID 11992422, compound

Product 1

HCID 11992612HCID 11992612, compoundYield 3.3%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

2,2-Dimethylpropyl 4-[4-(methoxycarbonyl)pyridin-2-yl]-1-piperazinecarboxylate (365 mg) obtained in Example 5 was dissolved in tetrahydrofuran (5 mL), and lithium tetrahydroborate (30 mg) was added thereto, stirred at room temperature for 30 minutes, and then 1 N sodium hydroxide was added thereto and stirred at room temperature for 30 minutes. The reaction liquid was diluted with ethyl acetate, washed with water and saturated saline water, and dried with anhydrous sodium sulfate. The solvent was evaporated away, and the resulting residue was isolated and purified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1) to obtain 11 mg of the entitled compound as a colorless oil.

Workup

  1. stirringstirred at room temperature for 30 minutes
  2. customThe reaction liquid
  3. washwashed with water and saturated saline water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe solvent was evaporated away
  6. customthe resulting residue was isolated
  7. custompurified through thin-layer silica gel chromatography (hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-2b277960b1f24c539aa5a9f6dda969ea
Source dataset
uspto-grants-2012_01
Patent number
US08101618B2

Reaction notes

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