Cyclohexane → 2-(Aminomethyl)adamantan-2-ol
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]2Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
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
- 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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