Carbamic acid, [(1R,3S)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester (9CI) Chemical Properties

Boiling point:

320.8±31.0 °C(Predicted)

Density 

1.08±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

12.27±0.40(Predicted)

Appearance

Off-white to light yellow Solid

optical activity

Consistent with structure

InChI

InChI=1S/C10H19NO3/c1-10(2,3)14-9(13)11-7-4-5-8(12)6-7/h7-8,12H,4-6H2,1-3H3,(H,11,13)/t7-,8+/m1/s1

InChIKey

SBUKINULYZANSP-SFYZADRCSA-N

SMILES

C(OC(C)(C)C)(=O)N[C@@H]1CC[C@H](O)C1

CAS DataBase Reference

225641-84-9

Carbamic acid, [(1R,3S)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester (9CI) Usage And Synthesis

Uses

Carbamic acid, [(1R,3S)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester (9CI) is carboxylic acid ester organic compounds, which can be used as pharmaceutical intermediates.

Synthesis

General procedure for the synthesis of tert-butyl ((1R,3S)-3-hydroxycyclopentyl)carbamate from (1S,4R)-4-cyclopenten-1-ol-2-amino-tert-butyloxycarbonyl: Tert-butyl (1S,4R)-4-hydroxycyclopent-2-enylcarbamate (2.0 g, 10 mmol) was dissolved in methanol (20 mL), and the reaction flask was subjected to three times nitrogen Displacement. 10% Pd/C catalyst (0.2 g, 10%, w/w) was added to the above solution, followed by three displacements with hydrogen. The reaction mixture was stirred at room temperature and hydrogen atmosphere (1 atm) for 14 hours. Upon completion of the reaction, the catalyst was removed by diatomaceous earth filtration. The filtrate was concentrated to afford the target product ((1R,3S)-3-hydroxycyclopentyl)carbamic acid tert-butyl ester (1.9 g, yield: 95%).

References

[1] Patent: US2016/200730, 2016, A1. Location in patent: Paragraph 0500; 0501

Carbamic acid, [(1R,3S)-3-hydroxycyclopentyl]-, 1,1-dimethylethyl ester (9CI)(225641-84-9)Related Product Information

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