Aluminium lithium hydride → HCID 59437169, compound

HRID 75165Notes

Reaction equation

HRID 75165 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH:7][CH:8]([CH3:24])[CH2:9][CH2:10][NH:11][C:12]([C:14]12[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2)=O>C1COCC1>[C:14]12([CH2:12][NH:11][CH2:10][CH2:9][CH:8]([OH:7])[CH3:24])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 59437164N-(3-hydroxybutyl)adamantane-1-carboxamide

Product 1

HCID 59437169HCID 59437169, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of LiAlH4 (51 mg, 1.36 mmol) in THF (1.5 mL) was added a solution of N-(3-hydroxybutyl)adamantane-1-carboxamide (170 mg, 0.68 mmol) in THF at 0° C. The mixture was stirred and heated under reflux overnight. The reaction was quenched with H2O (2 mL). The mixture was filtered to give 4-(1-adamantylmethylamino)butan-2-ol (50 mg, 31%). 1H NMR (CD3OD, 400 MHZ): δ=1.12 (d, 3H), 1.58˜1.88 (m, 17H) 2.28 (t, 2H), 2.65 (m, 2H), 3.79 (m, 1H).

Workup

  1. temperatureheated
  2. temperatureunder reflux overnight
  3. customThe reaction was quenched with H2O (2 mL)
  4. filtrationThe mixture was filtered

Sources & evidence

ORD record
ord-7d0004d4b90540a4b458425b512e3de6
Source dataset
uspto-grants-2014_09
Patent number
US08835426B2

Reaction notes

Loading…