Methanol → 2-(2-hydroxyethoxy)acetic acid N-[2-(1-adamantyl)ethyl]-1-pentylamide
Reaction equation
[BH4-].[Na+].[C:3]12([CH2:13][CH2:14][N-:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[CH2:12][CH:7]3[CH2:8][CH:9]([CH2:11][CH:5]([CH2:6]3)[CH2:4]1)[CH2:10]2.[OH2:21].[C:22]([O:25][CH2:26][CH3:27])(=O)[CH3:23].C[OH:29]>>[C:3]12([CH2:13][CH2:14][N:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])[C:23](=[O:29])[CH2:22][O:25][CH2:26][CH2:27][OH:21])[CH2:10][CH:9]3[CH2:8][CH:7]([CH2:6][CH:5]([CH2:11]3)[CH2:4]1)[CH2:12]2Participants
Procedure
Next, sodium borohydride (0.18 g, 4.8 mmol) was added to a solution of N-[2-(1-adamantyl)ethyl]-1-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 and then distributed between water (20 ml) and ethyl acetate (30 ml). 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 obtained residue was purified by silica gel column chromatography to give 2-(2-hydroxyethoxy)acetic acid N-[2-(1-adamantyl)ethyl]-1-pentylamide (74 mg, 22%) as an oily matter.
Workup
- temperaturecooling
- stirringthe whole was stirred for 10 minutes
- washThe organic layer was washed with a saturated aqueous sodium chloride solution (10 ml)
- dry with materialdried over anhydrous magnesium sulfate
- customThe solvent was evaporated under reduced pressure
- customthe obtained residue was purified by silica gel column chromatography
Sources & evidence
- ORD record
- ord-6ed94ec4435249158514bf72f8c4a981
- Source dataset
- uspto-grants-2010_06
- Patent number
- US07741346B2
Reaction notes
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