Aluminium lithium hydride → HCID 66757609, compound

HRID 242606Notes

Reaction equation

HRID 242606 reaction equation
C([O:3][C:4](=O)[C:5]([O:8][C:9]1[CH:42]=[CH:41][C:12]2[O:13][CH2:14][C:15]3[N:40]=[CH:39][CH:38]=[CH:37][C:16]=3[C:17](=[CH:18][CH2:19][CH2:20][N:21]3[CH2:26][CH2:25][C:24]([C:28]4[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=4)([OH:27])[C:23]([CH3:36])([CH3:35])[CH2:22]3)[C:11]=2[CH:10]=1)([CH3:7])[CH3:6])C.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1.C(OCC)(=O)C>[Cl:34][C:31]1[CH:32]=[CH:33][C:28]([C:24]2([OH:27])[CH2:25][CH2:26][N:21]([CH2:20][CH2:19][CH:18]=[C:17]3[C:16]4[CH:37]=[CH:38][CH:39]=[N:40][C:15]=4[CH2:14][O:13][C:12]4[CH:41]=[CH:42][C:9]([O:8][C:5]([CH3:6])([CH3:7])[CH2:4][OH:3])=[CH:10][C:11]3=4)[CH2:22][C:23]2([CH3:36])[CH3:35])=[CH:29][CH:30]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66758952HCID 66758952, compound

Product 1

HCID 66757609HCID 66757609, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a cooled (0° C.) solution of 2-(5-{3-[4-(4-Chloro-phenyl)-4-hydroxy-3,3-dimethyl-piperidin-1-yl]-propylidene}-5,11-dihydro-10-oxa-1-aza-dibenzo[a,d]cyclohepten-7-yloxy)-2-methyl-propionic acid ethyl ester (117 mg, 0.193 mmol) in tetrahydrofuran (5 mL) was added lithium aluminum hydride (1.0 M solution in tetrahydrofuran, 0.39 mL, 0.39 mmol). The reaction was allowed to stir at 0° C. for 2 h. Excess hydride was quenched by the addition of a saturated aqueous potassium/sodium tartrate solution. The mixture was stirred at rt until two clear phases formed. The mixture was diluted with ethyl acetate and shaken. The extracts were dried over magnesium sulfate, filtered and concentrated. The crude residue was purified by silica gel chromatography (methylene chloride—90:10 methylene chloride/methanol gradient) to afford the titled compound (102 mg, 94%).

Workup

  1. customExcess hydride was quenched by the addition of a saturated aqueous potassium/sodium tartrate solution
  2. stirringThe mixture was stirred at rt until two clear phases
  3. customformed
  4. stirringshaken
  5. dry with materialThe extracts were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe crude residue was purified by silica gel chromatography (methylene chloride—90:10 methylene chloride/methanol gradient)

Sources & evidence

ORD record
ord-e309996194bf4c20980d8ad8262d95c8
Source dataset
uspto-grants-2014_02
Patent number
US08653096B2

Reaction notes

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