Description

rac-tert-butyl (1R,4R,5S)-5-amino-2-azabicyclo[2.1.1]hexane-2-carboxylate (CAS: 1027177-72-5) is a high-purity bicyclic organic compound with the molecular formula C₁₀H₁₈N₂O₂. This stereochemically defined building block features a rigid azabicyclo[2.1.1]hexane core with tert-butoxycarbonyl (Boc) protection at the nitrogen and a primary amine at the 5-position. The compound is supplied as a racemic mixture of enantiomers, with the (1R,4R,5S) configuration explicitly indicated for one enantiomer. Its unique strained bicyclic structure makes it particularly valuable for medicinal chemistry applications where conformational restriction is desired. The Boc protecting group enables selective deprotection under mild acidic conditions for further functionalization. This product is rigorously characterized by ¹H NMR, ¹³C NMR, HPLC, and mass spectrometry to ensure ≥95% purity, making it suitable for pharmaceutical research and asymmetric synthesis.

Properties

• CAS Number: 1027177-72-5
• Complexity: 259
• IUPAC Name: tert-butyl (1S,4S,5R)-5-amino-2-azabicyclo[2.1.1]hexane-2-carboxylate
• InChI: InChI=1S/C10H18N2O2/c1-10(2,3)14-9(13)12-5-6-4-7(12)8(6)11/h6-8H,4-5,11H2,1-3H3/t6-,7-,8+/m0/s1
• InChI Key: MVDURHAWUZLLLY-BIIVOSGPSA-N
• Exact Mass: 198.136827821
• Molecular Formula: C10H18N2O2
• Molecular Weight: 198.26
• SMILES: CC(C)(C)OC(=O)N1C[C@@H]2C[C@H]1[C@@H]2N
• Topological: 55.6
• Monoisotopic Mass: 198.136827821
• Synonyms: 1403766-80-2, rac-tert-butyl (1R,4R,5S)-5-amino-2-azabicyclo[2.1.1]hexane-2-carboxylate, rac-tert-butyl (1R,4R,5S)-5-amino-2-azabicyclo(2.1.1)hexane-2-carboxylate, 845-476-8, 1027177-72-5, tert-butyl (1S,4S,5R)-5-amino-2-azabicyclo[2.1.1]hexane-2-carboxylate, MFCD16294635, (1S,4S,5R)-tert-Butyl 5-amino-2-azabicyclo[2.1.1]hexane-2-carboxylate, tert-butyl endo-5-amino-2-azabicyclo[2.1.1]hexane-2-carboxylate, AKOS040767971, AS-84780, E73628, EN300-6732464, EN300-19657798, (1S,4S,5R)-2-Boc-5-amino-2-azabicyclo[2.1.1]hexane, tert-Butyl(1S,4S,5R)-5-amino-2-azabicyclo[2.1.1]hexane-2-carboxylate, tert-Butyl rac-(1S,4S,5R)-5-amino-2-azabicyclo[2.1.1]hexane-2-carboxylate

Application

This compound serves as a valuable scaffold in medicinal chemistry for the development of conformationally restricted drug candidates, particularly for CNS targets. The strained azabicyclo[2.1.1]hexane core provides unique three-dimensionality to enhance binding selectivity in drug discovery. The Boc-protected amine allows for selective deprotection and subsequent derivatization, making it useful in parallel synthesis approaches. Researchers utilize this building block in fragment-based drug design and as a rigid spacer in peptidomimetics.

Safety and Hazards

GHS Hazard Statements

• H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
• H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]
• H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
• H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Precautionary Statements

• P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501

Hazard Classes and Categories

• Acute Tox. 4 (100%)
• Skin Irrit. 2 (100%)
• Eye Irrit. 2A (100%)
• STOT SE 3 (100%)

If you are interested or have any questions, please contact us at support@atomfair.com

Disclaimer: Sold exclusively for laboratory research. Prohibited for commercial use, diagnostics, or human/animal applications. Buyers assume all compliance liability.