Cyclohexane → 2-Aminomethyl-adamantan-2-ol

HRID 745854Notes

Reaction equation

HRID 745854 reaction equation
[C:1]([C:3]1([OH:13])[CH:10]2[CH2:11][CH:6]3[CH2:7][CH:8]([CH2:12][CH:4]1[CH2:5]3)[CH2:9]2)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].C1CCCCC1>CCOCC>[NH2:2][CH2:1][C:3]1([OH:13])[CH:4]2[CH2:12][CH:8]3[CH2:7][CH:6]([CH2:11][CH:10]1[CH2:9]3)[CH2:5]2

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 34511512-Hydroxytricyclo[3.3.1.13,7]decane-2-carbonitrileHCID 21226445Aluminium lithium hydride

Product 1

HCID 2866492-Aminomethyl-adamantan-2-olYield 75.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of 2-cyanoadamantan-2-ol (6.0 grams, 0.03 mol) in ether was added to a suspension of lithium aluminum hydride (3.9 grams, 0.13 mol) in ether. The reaction mixture was refluxed for 6 hours. Following workup, 4.10 grams of 2-aminomethyl-2-hydroxyadamantane were obtained as white crystals, melting point 154°-156° C. (cyclohexane).

Workup

  1. temperatureThe reaction mixture was refluxed for 6 hours

Sources & evidence

ORD record
ord-d43b9761446f42fc90e3256804017ad9
Source dataset
uspto-grants-1986_07
Patent number
US04600782

Reaction notes

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