trans-4-Aminoadamantan-1-ol
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trans-4-Aminoadamantan-1-ol
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CAS No:
62058-03-1
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Formula:
C10H17NO
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Chemical Name:
trans-4-Aminoadamantan-1-ol
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CAS No:
trans-4-Aminoadamantan-1-ol Use and Manufacturing
General procedure: To a solution of 9 (247 mg, 0.82 mmol) in MeOH (5 mL) was added10percent palladim on carbon (50percent wet) (87 mg, 0.08 mmol), and the reactionmixture was stirred at room temperature for 5 h under hydrogenatmosphere. After 10percent palladim on carbon was filtered off with Celite, the filtrate was concentrated under reduced pressure to give the titlecompound (135 mg, 98percent), which was used in the next reaction withoutfurther purification. 1H NMR (CD3OD) delta 1.39'1.46 (m, 2H), 1.70'1.81(m, 6H), 1.90'1.98 (m, 4H), 2.03'2.08 (m, 1H), 2.93'2.98 (m, 1H); MS(ESI) m/z 168 [M+H]+.General procedure: Under a nitrogen atmosphere, a mixture of 6 (2.5 g, 12.8 mmol), 11(3.2 g, 19.2 mmol) and n-Bu3N (9.1 mL, 38.3 mmol) in NMP (12.5 mL)was stirred at a bath temperature of 200 °C for 2.5 h. After cooling toroom temperature, the reaction solution was added dropwise to H2O/Et2O while stirring. The obtained solid was collected by filtration, washed with H2O and Et2O, and then dried. The obtained solid waswarmed and dissolved in MeOH, and filtered while warming. The filtratewas concentrated under reduced pressure. To the residue wasadded MeOH, and the mixture was heated and dissolved. After coolingto room temperature, the solution was stirred overnight at room temperature.The precipitated solid was collected by filtration, washedMeOH, and dried under reduced pressure to give the title compound(2.1 g, 50percent). 1H NMR (DMSO-d6) delta 1.37'1.46 (m, 2H), 1.62'1.73 (m, 4H), 1.80'1.89 (m, 4H), 2.02'2.08 (m, 1H), 2.12'2.18 (m, 2H), 4.10'4.17 (m, 1H), 4.51 (s, 1H), 6.41 (d, J=3.6 Hz, 1H), 6.88'7.10(br, 1H), 7.13 (d, J=3.6 Hz, 1H), 7.65'7.90 (br, 1H), 8.38 (s, 1H), 10.10 (d, J=8.0 Hz, 1H), 11.45 (br s, 1H); MS (ESI) m/z 327 [M+H]+;Anal. Calcd for C18H22N4O2·H2O: C, 62.77; H, 7.02; N, 16.27. Found: C, 62.39; H, 7.04; N, 16.14.
Computed Properties
Molecular Weight:167.25
XLogP3:0.4
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:2
Exact Mass:167.131014166
Monoisotopic Mass:167.131014166
Topological Polar Surface Area:46.2
Heavy Atom Count:12
Complexity:200
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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