ChemicalBook CAS DataBase List (1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carboxamide methanesulfonate

(1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carboxamide methanesulfonate synthesis

6synthesis methods

Product Name:(1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carboxamide methanesulfonate
CAS Number:709031-45-8
Molecular formula:C7H14N2O4S
Molecular Weight:222.26

75-75-2 Synthesis

75-75-2
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361440-67-7 Synthesis

(1S,3S,5S)-3-(Aminocarbonyl)-2-azabicyclo[3.1.0]hexane-2-carboxylic acid tert-butyl ester

361440-67-7
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(1S,3S,5S)-2-Azabicyclo[3.1.0]hexane-3-carboxamide methanesulfonate

709031-45-8
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Yield: 96.7%

Reaction Conditions:

in isopropyl alcohol at 60 - 70; for 5 h;

Steps:

3 Example 3 Preparation of methanesulfonic acid salt of (lS,3S,5S)-2-azabicyclo[3.1.0]hexane-3- carboxamide
Example 3 Preparation of methanesulfonic acid salt of (lS,3S,5S)-2-azabicyclo[3.1.0]hexane-3- carboxamide Tert-butyl (lS,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hexane-2-carboxylate (100 g, 0.442 mole) was combined with isopropyl alcohol (600 ml), with stirring at 25-30°C. The mixture was heated to 60-70°C and methanesulfonic acid (55.2 g, 0.575 mole) was added in small amounts over 60 minutes. The mixture was stirred for 4 hours at 60-70°C. Completion of the reaction was confirmed using TLC. The mixture was cooled to 5-15°C and stirred for 1 hour. The mixture was filtered and the solid was washed with chilled isopropyl alcohol (2x50 ml). The filtrate was dried under vacuum to obtain the methanesulfonic acid salt of (lS,3S,5S)-2- azabicyclo[3.1.0]hexane-3-carboxamide. (Yield=96.7%; HPLC purity= 96%) Mass: 434 [M+H]⁺ 1H-NMR (CDCI₃) δ: 6.96 (1 H, s), 5.68 (1 H, s), 5.39-5.42 (1 H, d), 4.88-4.91 (1 H, dd), 4.52- 4.54 (1 H, d), 3.67-3.70 (1 H, m), 2.50-2.53 (1 H, dd), 2.22 (2 H, s), 2.03 (1 H, s), 1.47-1.75 (15 H, m), 1.41 (9 H, s), 1.24 (1 H, s), 0.81-0.95 (2 H, m)

References:

AMNEAL PHARMACEUTICALS LLC;KUMAR, Agarwal Virendra;BADRULHUSAN, Siddiqui Arif;KESHAV, Kataria Lalit;SUBODHBHAI, Maheta Abhay;CHANGANBHAI, Butani Pankaj;PRABHAKARRAO, Patil Shashikant;YASHWANT, Patil Tushar;SURYAKANT, Deore Ganesh;JAHYANTIBHAI, Pansuriya Ketan;SURESHBHAI, Patel Hitesh;BADHABHAI, Sondharava Lalit WO2015/31595, 2015, A1 Location in patent:Page/Page column 11; 12