Water → HCID 59437180, compound

HRID 75155

Reaction equation

HRID 75155 reaction equation
[C:1]12([CH2:11][NH:12][C:13](=O)[CH2:14][C:15](=[O:20])[CH2:16][CH:17]([CH3:19])[CH3:18])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[H-].[H-].[H-].[H-].[Li+].[Al+3].O.[OH-].[Na+]>C1COCC1>[C:1]12([CH2:11][NH:12][CH2:13][CH2:14][CH:15]([OH:20])[CH2:16][CH:17]([CH3:18])[CH3:19])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59437162N-(1-adamantylmethyl)-5-methyl-3-oxohexanamide

Product 1

HCID 59437180HCID 59437180, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of N-(1-adamantylmethyl)-5-methyl-3-oxohexanamide (1.5 g, 5.1 mmol) in anhydrous THF (15 mL) was added slowly to a suspension of LAH (500 mg, 13.1 mmol) in anhydrous THF (5 mL) under N2 at 0° C. The reaction mixture was heated to 70° C. and stirred at this temperature overnight. Water (0.5 mL) and 10% aq NaOH (0.5 mL) were added to quench the reaction. The resulting slurry was filtered. The filtrate was concentrated in vacuo and the residue was purified by chromatography on a silica gel column eluted with 10:1 PE/EtOAc to give 1-(1-adamantylmethylamino)-5-methylhexan-3-ol (900 mg, 63.3%). MS (M+1): 280.

Workup

  1. customto quench
  2. customthe reaction
  3. filtrationThe resulting slurry was filtered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by chromatography on a silica gel column
  6. washeluted with 10:1 PE/EtOAc

Sources & evidence

ORD record
ord-3a0ef8e6fb3944ec947316a942c21f3d
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Linked notes

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