Sodium Hydroxide → (Azepan-4-yl)methanol

HRID 1620560Notes

Reaction equation

HRID 1620560 reaction equation
O=[C:2]1[NH:8][CH2:7][CH2:6][CH:5]([C:9]([O-])=[O:10])[CH2:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-].[OH-].[Na+]>C1COCC1.O>[NH:8]1[CH2:2][CH2:3][CH2:4][CH:5]([CH2:9][OH:10])[CH2:6][CH2:7]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 866787397-Oxoazepane-4-carboxylate

Product 1

HCID 22594076(Azepan-4-yl)methanolYield 84.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
60 °C

Procedure

A solution of the obtained 7-oxoazepane-4-carboxylate (2.02 g) in THF (29 mL) was added dropwise to a suspension of lithium aluminum hydride (2.07 g) in THF (80 mL) under ice-cooling. The reaction mixture was stirred at room temperature for 3 hr and at 60° C. overnight. The reaction mixture was ice-cooled, diluted with THF (200 mL), and water (2.02 mL) was slowly added dropwise. Furthermore, 15% aqueous sodium hydroxide solution (2.02 mL) was added dropwise, then water (4.04 mL) was added, and the mixture was stirred at room temperature for 3 hr. The solid was separated by filtration, and the filtrate was concentrated under reduced pressure to give the title compound (1.41 g).

Workup

  1. temperaturecooling
  2. temperaturecooled
  3. additionwas slowly added dropwise
  4. stirringthe mixture was stirred at room temperature for 3 hr
  5. customThe solid was separated by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-956f31ec38a747649b20433590197912
Source dataset
uspto-grants-2014_07
Patent number
US08772277B2

Reaction notes

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