Water → 2-(2-hydroxyethoxy)acetic acid N-[2-(1-adamantyl)ethyl]-1-pentylamide

HRID 11487Notes

Reaction equation

HRID 11487 reaction equation
[BH4-].[Na+].[C:3]12([CH2:13][CH2:14][N:15]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:16](=[O:24])[CH2:17][O:18][CH2:19][C:20](OC)=[O:21])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.O.C(OCC)(=O)C>CO>[C:3]12([CH2:13][CH2:14][N:15]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[C:16](=[O:24])[CH2:17][O:18][CH2:19][CH2:20][OH:21])[CH2:10][CH:9]3[CH2:8][CH:7]([CH2:6][CH:5]([CH2:11]3)[CH2:4]1)[CH2:12]2

Participants

6

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 574812732-methoxycarbonylmethoxyacetic acid N-[2-(1-adamantyl) ethyl]-N-pentylamide

Product 1

HCID 574812742-(2-hydroxyethoxy)acetic acid N-[2-(1-adamantyl)ethyl]-1-pentylamideYield 22%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Next, sodium borohydride (0.18 g, 4.8 mmol) was added to a solution of 2-methoxycarbonylmethoxyacetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide (0.37 g, 0.96 mmol) in methanol (3 ml) under ice-cooling, and the mixture was stirred at room temperature overnight. Water (10 ml) was added to the reaction mixture, and the whole was stirred for 10 minutes. Then, water (20 ml) and ethyl acetate (30 ml) were added thereto, and layers were separated. The organic layer was washed with a saturated aqueous sodium chloride solution (10 ml) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the resulting residue was purified by silica gel column chromatography to give 74 mg (22%) of 2-(2-hydroxyethoxy)acetic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide as an oily matter.

Workup

  1. temperaturecooling
  2. stirringthe whole was stirred for 10 minutes
  3. customlayers were separated
  4. washThe organic layer was washed with a saturated aqueous sodium chloride solution (10 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated under reduced pressure
  7. customthe resulting residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-2c635ed316974a799655bfc4decc52db
Source dataset
uspto-grants-2006_08
Patent number
US07098226B2

Reaction notes

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