HCID 15129660, compound → HCID 12017123, compound

HRID 399444Notes

Reaction equation

HRID 399444 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=3)[C:10]=2[C:21]([C:23]2[CH:28]=[CH:27][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:25][CH:24]=2)=[O:22])=[CH:5][CH:4]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[CH2:18][CH2:17][C:16]3[C:11](=[CH:12][CH:13]=[C:14]([O:19][CH3:20])[CH:15]=3)[C:10]=2[CH:21]([C:23]2[CH:24]=[CH:25][C:26]([O:29][CH2:30][CH2:31][N:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:27][CH:28]=2)[OH:22])=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 15129660HCID 15129660, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12017123HCID 12017123, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4.45 g (0.009 mol) of [2-(4-methoxyphenyl)-3,4-dihydro-6-methoxynaphth-1-yl][4-(1-piperidinyl-2-ethoxy) phenyl] methanone was dissolved in 100 mL of THF and 1 g (0.026 mol) of LiAlH4 was carefully added. The reaction mixture was stirred at room temperature and under N2 for eighteen hours. The reaction mixture was evaporated to dryness and 100 mL of water was carefully added. The reaction mixture was extracted twice with 100 mL portions of EtOAc. The combind EtOAc extracts were dried by filteration through anhydrous Na2SO4. The EtOAc extract was evaporated to dryness in vacuo. This yielded 3.38 g of the title compound as a white, amorphous powder.

Workup

  1. customThe reaction mixture was evaporated to dryness and 100 mL of water
  2. additionwas carefully added
  3. extractionThe reaction mixture was extracted twice with 100 mL portions of EtOAc
  4. dry with materialThe combind EtOAc extracts were dried by filteration through anhydrous Na2SO4
  5. extractionThe EtOAc extract
  6. customwas evaporated to dryness in vacuo

Sources & evidence

ORD record
ord-be3f4ab2210849d1bf55d9ced5aadbfb
Source dataset
uspto-grants-1998_10
Patent number
US05821253

Reaction notes

Loading…