Aluminium lithium hydride → HCID 69799954, compound

HRID 1064382Notes

Reaction equation

HRID 1064382 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[C:7]1([CH:13]2[CH2:18][CH2:17][N:16]([C:19]([CH:21]3[CH2:27][CH2:26][C:25]4[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=4[C:23](=[O:32])[CH2:22]3)=O)[CH2:15][CH2:14]2)[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>CCOCC>[C:7]1([CH:13]2[CH2:14][CH2:15][N:16]([CH2:19][C@@H:21]3[CH2:27][CH2:26][C:25]4[CH:28]=[CH:29][CH:30]=[CH:31][C:24]=4[C@H:23]([OH:32])[CH2:22]3)[CH2:17][CH2:18]2)[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22273746HCID 22273746, compound

Product 1

HCID 69799954HCID 69799954, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.15 g (3.8 mmol) of LiAlH4 were added to a solution of 0.33 g (0.95 mmol) of (±)-7-[(4-phenylpiperidin-1-yl)carbonyl]-6,7,8,9-tetrahydro-5H-benzocyclohepten-5-one in 15 mL of dry Et2O at 0° C. and the resulting mixture was heated to reflux overnight. After cooling, the reaction was quenched by the careful addition of 0.5 mL of 2 N NaOH, the suspension was stirred 10 min and then filtered by suction on a Celite pad washing with Et2O. The solvent was removed in vacuo, yielding 0.25 g of the title compound. m.p.=48-50° C.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux overnight
  3. temperatureAfter cooling
  4. customthe reaction was quenched by the careful addition of 0.5 mL of 2 N NaOH
  5. filtrationfiltered by suction on a Celite pad
  6. washwashing with Et2O
  7. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-ebf67839e58a435cb4f61aa758423f8b
Source dataset
uspto-grants-2005_11
Patent number
US06969724B2

Reaction notes

Loading…