Methanol → N-heptyl-N-ethyl(6-hydroxy)hexanamide

HRID 439760Notes

Reaction equation

HRID 439760 reaction equation
[CH2:1]([N:8]([CH2:19][CH3:20])[C:9](=[O:18])[CH2:10][CH2:11][CH2:12][CH2:13][C:14](OC)=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7].[BH4-].[Na+].CO>C(O)(C)(C)C>[CH2:1]([N:8]([CH2:19][CH3:20])[C:9](=[O:18])[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][OH:15])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 86748668N-heptyl-N-ethyladipamic acid, methyl ester

Product 1

HCID 22407916N-heptyl-N-ethyl(6-hydroxy)hexanamideYield 35.8%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A mixture of a solution of 3.1 gms of the N-heptyl-N-ethyladipamic acid, methyl ester in 40 ml of tert-butanol and 800 mg of sodium borohydride is heated to reflux, following which 7.8 ml of methanol is added dropwise. The reaction mixture is stirred at reflux for 18 hours and then partitioned between water and CH2Cl2. After separation, the organic layer is dried over MgSO4, filtered, and concentrated under vacuum. The residue obtained is flash chromatographed on normal phase silica gel with a 4/1 ratio of hexane and ethyl acetate to yield 1.0 gms of N-heptyl-N-ethyl (6-hydroxy)hexanamide.

Workup

  1. temperatureis heated
  2. temperatureto reflux
  3. additionis added dropwise
  4. temperatureat reflux for 18 hours
  5. custompartitioned between water and CH2Cl2
  6. customAfter separation
  7. dry with materialthe organic layer is dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under vacuum
  10. customThe residue obtained
  11. customchromatographed on normal phase silica gel with a 4/1 ratio of hexane and ethyl acetate

Sources & evidence

ORD record
ord-bf7aa1f34dd244909b91280f5fb6b98a
Source dataset
uspto-grants-1996_05
Patent number
US05516767

Reaction notes

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