Tetrahydrofuran → HCID 20244239, compound

HRID 483011Notes

Reaction equation

HRID 483011 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].O1CCCC1.[OH:12][C:13]1[CH:22]=[C:21]([O:23][CH:24]([CH2:26][CH2:27][CH2:28][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH3:25])[CH:20]=[C:19]2[C:14]=1[CH:15]([CH2:39][CH2:40][C:41]#[N:42])[CH2:16][CH:17]1[CH2:38][CH2:37][CH2:36][CH2:35][N:18]12>C(OCC)(=O)C>[OH:12][C:13]1[CH:22]=[C:21]([O:23][CH:24]([CH2:26][CH2:27][CH2:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH3:25])[CH:20]=[C:19]2[C:14]=1[CH:15]([CH2:39][CH2:40][CH2:41][NH2:42])[CH2:16][CH:17]1[CH2:38][CH2:37][CH2:36][CH2:35][N:18]12

Participants

5

Reactant 3

HCID 8028Tetrahydrofuran2×HCID 20244227HCID 20244227, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 20244239HCID 20244239, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Under anhydrous conditions and a nitrogen atmosphere, to a solution of 190 mg. (5 mmole) lithium aluminum hydride in 50 ml. tetrahydrofuran at 10° C. is added dropwise a solution of 2.09 g. (5 mmole) dl-7-hydroxy-6-(2-cyanoethyl)-9-(5-phenyl-2-pentyloxy)-2,3,4,4a,5,6-hexahydro-1H-pyrido[1,2-a]quinoline in 25 ml. tetrahydrofuran. The mixture is stirred at room temperature for 6 hours after the addition. Ethyl acetate is added to quench the reaction, the solvent is evaporated in vacuo and the residue partitioned between water and methylene chloride. The organic extracts are dried (MgSO4) and the solvent evaporated to provide the title compound as the free base.

Workup

  1. additionafter the addition
  2. customto quench
  3. customthe reaction
  4. customthe solvent is evaporated in vacuo
  5. customthe residue partitioned between water and methylene chloride
  6. dry with materialThe organic extracts are dried (MgSO4)
  7. customthe solvent evaporated

Sources & evidence

ORD record
ord-19898148737b45bdb3b0c32c2472554b
Source dataset
uspto-grants-1986_03
Patent number
US04576964

Reaction notes

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