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18162-48-6872-50-4Methylene ChloridenaphthaleneTHFTitanium Dioxide
ChemicalBook CAS DataBase List Carbamic acid, [(1S,3R)-3-(hydroxymethyl)cyclopentyl]-, 1,1-dimethylethyl
664341-72-4

Carbamic acid, [(1S,3R)-3-(hydroxymethyl)cyclopentyl]-, 1,1-dimethylethyl synthesis

9synthesis methods
(6R,7S)-2-BOC-2-AZA-BICYCLO[2.2.1]HEPT-5-EN-3-ONE

151792-53-9
47 suppliers
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Carbamic acid, [(1S,3R)-3-(hydroxymethyl)cyclopentyl]-, 1,1-dimethylethyl

664341-72-4
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Yield: 80%

Reaction Conditions:

with sodium tetrahydroborate in methanol at 25; for 3 h;Inert atmosphere;

Steps:

((1R,3S)-3-Aminocyclopentyl)methanol (4)
A mixture of 3 (15.68g, 74.25mmol) and NaBH4 (5.62g, 14.85mmol) in MeOH (300mL) was stirred at 25°C for 3h. The solvents were removed in vacuo, and the residue was partitioned between EtOAc and H2O. The organic layer was washed with brine, dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified by column chromatography (silica gel, hexanes/EtOAc, 2/1) to afford the Boc-protected amino alcohol (12.79g, 80%) as a white solid: 1H NMR (400MHz, CDCl3) δ 3.90 (br s, 1H), 3.56 (d, J=5.0Hz, 2H), 2.19-2.10 (m, 2H), 1.92-1.83 (m, 1H), 1.74-1.71 (m, 1H), 1.47-1.42 (m, 2H), 1.40 (s, 9H), 1.14-1.10 (m, 1H); [Boc Deprotection] A solution of the Boc-protected amino alcohol (12.79g, 59.44mmol) in H2O (700mL) was stirred at 100°C for 20h. The solvents were removed to give the amino alcohol 4 [30] (5.47g, 80%) as a white solid: 1H NMR (400MHz, CDCl3) δ 3.58-3.46 (m, 3H), 2.75 (br s, 2H), 2.40-2.30 (m, 1H), 1.99-1.92 (m, 1H), 1.80-1.69 (m, 3H), 1.50-1.45 (m, 1H), 1.38-1.28 (m, 1H); HRMS (ESI) m/z 116.1073 [(M+H)+ calcd for C6H13NO 116.1069].

References:

Kwak, Seung-Hwa;Lim, Won Young;Hao, Aili;Mashalidis, Ellene H.;Kwon, Do-Yeon;Jeong, Pyeonghwa;Kim, Mi Jung;Lee, Seok-Yong;Hong, Jiyong [European Journal of Medicinal Chemistry,2021,vol. 215,art. no. 113272]

204913-00-8 Synthesis
2-Azabicyclo[2.2.1]heptane-2-carboxylic acid, 3-oxo-, 1,1-dimethylethyl ester, (1S)-

204913-00-8
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Carbamic acid, [(1S,3R)-3-(hydroxymethyl)cyclopentyl]-, 1,1-dimethylethyl

664341-72-4
24 suppliers
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References
(-)-(1R,3S)-N-Boc-3-Aminocyclopentanecarboxylic acid

161660-94-2
157 suppliers
$21.00/250mg

Carbamic acid, [(1S,3R)-3-(hydroxymethyl)cyclopentyl]-, 1,1-dimethylethyl

664341-72-4
24 suppliers
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References
79200-56-9 Synthesis
((1R,4S)-2-Azabicyclo[2.2.1]hept-5-en-3-one

79200-56-9
226 suppliers
$10.00/1g

Carbamic acid, [(1S,3R)-3-(hydroxymethyl)cyclopentyl]-, 1,1-dimethylethyl

664341-72-4
24 suppliers
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References
(1S,4R)-2-AZABICYCLO[2.2.1]HEPTAN-3-ONE

134003-03-5
18 suppliers
$733.72/250MG

Carbamic acid, [(1S,3R)-3-(hydroxymethyl)cyclopentyl]-, 1,1-dimethylethyl

664341-72-4
24 suppliers
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References

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