Water → HCID 11279224, compound

HRID 1182081Notes

Reaction equation

HRID 1182081 reaction equation
C([O:3][C:4](=O)[CH2:5][CH2:6][CH2:7][N:8]1[CH2:13][CH2:12][CH:11]([O:14][CH:15]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)C.[H-].[H-].[H-].[H-].[Li+].[Al+3].O>CCOCC>[CH:15]([O:14][CH:11]1[CH2:12][CH2:13][N:8]([CH2:7][CH2:6][CH2:5][CH2:4][OH:3])[CH2:9][CH2:10]1)([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10429946Ethyl 4-(diphenylmethoxy)-1-piperidinebutanoateHCID 21226445Aluminium lithium hydride

Product 1

HCID 11279224HCID 11279224, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

The compound obtained from step 1 (0.4 g) was dissolved in ether, and cooled in an ice bath. LiAlH4 (0.1 g) was added slowly to the solution. The resulting mixture was reacted at room temperature for 1 hr. before adding water to end the reaction. The resulting solution was then extracted by using water and ester. An organic solution layer was dehydrated over magnesium sulfate, filtered, and concentrated under reduced pressure. The column chromatography was performed thereon, thereby obtaining crude yellowish liquid product (0.15, 43% yield) of the title.

Workup

  1. temperaturecooled in an ice bath
  2. customThe resulting mixture was reacted at room temperature for 1 hr
  3. customthe reaction
  4. extractionThe resulting solution was then extracted
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customobtaining crude yellowish liquid product (0.15, 43% yield) of the title

Sources & evidence

ORD record
ord-08de9f0e4a3b43f6bd746903f6ff8871
Source dataset
uspto-grants-2007_10
Patent number
US07288552B2

Reaction notes

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