Sodium Hydroxide → (1-Benzylazepan-3-yl)methanol

HRID 602119Notes

Reaction equation

HRID 602119 reaction equation
[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([C:15](OC)=[O:16])[C:9]1=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>O1CCCC1>[CH2:1]([N:8]1[CH2:14][CH2:13][CH2:12][CH2:11][CH:10]([CH2:15][OH:16])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 21902024Methyl 1-benzyl-2-oxoazepane-3-carboxylate

Product 1

HCID 21901990(1-Benzylazepan-3-yl)methanolYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 1-benzyl-2-oxoperhydroazepine-3-carboxylate (2.39 g, 9.15 mmol) was dissolved in tetrahydrofuran (50 mL). To this solution, lithium aluminum hydride (868 mg, 18.3 mmol) was added and the mixture was stirred for 2 hours while being refluxed. Subsequently, ice water and a 10% aqueous sodium hydroxide solution were added and the mixture was stirred at room temperature for 1 hour. The reaction mixture was then filtered through Celite. The filtrate was extracted with ethyl acetate and the extract washed with brine, followed by drying over magnesium sulfate and evaporation of the solvent. Purification of the residue by silica gel column chromatography (Chromatorex NH-DM2035 (Fuji Sylysia Chemical Co., Ltd.) hexane:ethyl acetate=20:1->3:1) gave 1.30 g (65%) of the desired compound as a colorless oil.

Workup

  1. temperaturewhile being refluxed
  2. stirringthe mixture was stirred at room temperature for 1 hour
  3. filtrationThe reaction mixture was then filtered through Celite
  4. extractionThe filtrate was extracted with ethyl acetate
  5. washthe extract washed with brine
  6. dry with materialby drying over magnesium sulfate and evaporation of the solvent
  7. customPurification of the residue by silica gel column chromatography (Chromatorex NH-DM2035 (Fuji Sylysia Chemical Co., Ltd.) hexane:ethyl acetate=20:1->3:1)

Sources & evidence

ORD record
ord-eb20ca407dc54af8a77dbf84661d7ebf
Source dataset
uspto-grants-2011_03
Patent number
US07902367B2

Reaction notes

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