Aluminium lithium hydride → 4-Aminotricyclo[3.3.1.13,7]decane-1-methanol

HRID 2194639Notes

Reaction equation

HRID 2194639 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].C[O:8][C:9]([C:11]12[CH2:20][CH:15]3[CH2:16][CH:17]([CH2:19][CH:13]([CH:14]3[NH2:21])[CH2:12]1)[CH2:18]2)=O>C1COCC1>[NH2:21][CH:14]1[CH:13]2[CH2:12][C:11]3([CH2:9][OH:8])[CH2:18][CH:17]([CH2:16][CH:15]1[CH2:20]3)[CH2:19]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57425932Methyl 4-aminoadamantane-1-carboxylate

Product 1

HCID 579281674-Aminotricyclo[3.3.1.13,7]decane-1-methanolYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Lithium aluminium hydride (5 g, 135 mmol) was added to a solution of 4-aminoadamantane-1-carboxylic acid methyl ester (5 g, 23.9 mmoles) in dry THF (100 ml) at 0-5° C. and the mixture heated under reflux for 3 h. It was then cooled to 0° C. and quenched with water (10 ml) followed by NaOH solution (20%, 12.5 ml). After stirring for 30 min, it was filtered through hyflo bed to remove inorganics. The clear filtrate was concentrated under reduced pressure and the residue triturated with hexane to give 4-amino-1-hydroxymethyladamantane (3.9 g, 90%). LC-MS (m/z): 182 (M+1). 1H NMR (300 MHz, DMSO-d6) δ 3.0 (d, 2H), 2.85 (b. s., 1H), 1.2-2.1 (13H, m).

Workup

  1. temperaturethe mixture heated
  2. temperatureunder reflux for 3 h
  3. customquenched with water (10 ml)
  4. filtrationit was filtered through hyflo bed
  5. customto remove inorganics
  6. concentrationThe clear filtrate was concentrated under reduced pressure
  7. customthe residue triturated with hexane

Sources & evidence

ORD record
ord-04b8d27b5c894ccc8081e57990bae418
Source dataset
uspto-grants-2012_12
Patent number
US08334305B2

Reaction notes

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