Water → HCID 22933843, compound

HRID 1269906Notes

Reaction equation

HRID 1269906 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH2:7]([N:14]1[CH2:20][CH2:19][CH2:18][CH2:17][C:16](=[O:21])[CH2:15]1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.O.[OH-].[Na+]>C(OCC)C>[CH2:7]([N:14]1[CH2:20][CH2:19][CH2:18][CH2:17][CH:16]([OH:21])[CH2:15]1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 151522641-Benzylazepan-3-oneHCID 21226445Aluminium lithium hydride

Product 1

HCID 22933843HCID 22933843, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Under a nitrogen atmosphere, lithium aluminum hydride (1.4 mg, 0.0369 mmol) was added to a solution of 1-benzylazepan-3-one (15 mg, 0.0738 mmol) in diethyl ether (1 ml) at 0° C., and the resulting mixture was heated to room temperature. After 30 minutes, water, a 2M-aqueous sodium hydroxide solution and water were added in that order to the reaction solution. The resulting mixture was filtered by the use of Celite, and the filtrate was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol) to obtain 1-benzylazepan-3-ol (16.2 mg, 100%).

Workup

  1. filtrationThe resulting mixture was filtered by the use of Celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customthe resulting residue was purified by a silica gel column chromatography (eluent: chloroform/methanol)

Sources & evidence

ORD record
ord-08a38b3988bf4c8bb4ddf16fb9941e07
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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