ChemicalBook CAS DataBase List Carbamic acid, [(1S,3R)-3-(hydroxymethyl)cyclopentyl]-, 1,1-dimethylethyl

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

9synthesis methods

Product Name:Carbamic acid, [(1S,3R)-3-(hydroxymethyl)cyclopentyl]-, 1,1-dimethylethyl
CAS Number:664341-72-4
Molecular formula:C11H21NO3
Molecular Weight:215.29

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

151792-53-9
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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]

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References

(-)-(1R,3S)-N-Boc-3-Aminocyclopentanecarboxylic acid

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References

79200-56-9 Synthesis

((1R,4S)-2-Azabicyclo[2.2.1]hept-5-en-3-one

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References

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References