3-Boc-6-oxa-3-aza-bicyclo[3.1.0]hexane Chemical Properties

Boiling point:

252.7±33.0 °C(Predicted)

Density 

1.181±0.06 g/cm3(Predicted)

refractive index 

1.4600 to 1.4640

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

powder to lump to clear liquid

pka

-0.98±0.20(Predicted)

color 

White or Colorless to Light yellow

InChI

InChI=1S/C9H15NO3/c1-9(2,3)13-8(11)10-4-6-7(5-10)12-6/h6-7H,4-5H2,1-3H3

InChIKey

NXZIGGBPLGAPTI-UHFFFAOYSA-N

SMILES

C12C(O1)CN(C(OC(C)(C)C)=O)C2

Safety Information

HazardClass 

IRRITANT

HS Code 

2934999090

3-Boc-6-oxa-3-aza-bicyclo[3.1.0]hexane Usage And Synthesis

Uses

6-Oxa-3-azabicyclo[3.1.0]hexane-3-carboxylic Acid tert-Butyl Ester, can be used as an intermediate in the synthesis of pharmaceutical products including inhibitors and anticancer compounds. It is used in the synthesis of chiral pyrrolidine Inhibitors with the ability to bind to Neuronal Nitric Oxide Synthase.

Synthesis

General procedure for the synthesis of 3-N-Boc-6-oxa-3-azabicyclo[3.1.0]hexane from N-Boc-3-pyrroline: compound 1 (N-Boc-3-pyrroline, 4.0 g, 0.024 mol) was dissolved in dichloromethane (40 mL) at room temperature followed by the addition of isochloroperoxybenzoic acid (m-CPBA, 0.3 mol) . The reaction mixture was stirred at room temperature for 12 hours. Upon completion of the reaction, the reaction was quenched with sodium sulfite (Na2SO3), followed by washing the organic layer with sodium bicarbonate (NaHCO3) solution. Finally, the organic phase was concentrated to give compound 2 (3-N-tert-butoxycarbonyl-6-oxa-3-azabicyclo[3.1.0]hexane, 4.4 g, 100% yield). The 1H NMR (400 MHz, CDCl3) data of compound 2 were as follows: δ 3.73 (multiple peaks, 2H), 3.60 (multiple peaks, 2H), 3.23 (multiple peaks, 2H), 1.37 (single peak, 9H).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 21, p. 4770 - 4773
[2] Patent: WO2013/96744, 2013, A1. Location in patent: Page/Page column 221
[3] Patent: US2007/37853, 2007, A1. Location in patent: Page/Page column 23
[4] Tetrahedron, 2003, vol. 59, # 49, p. 9729 - 9742
[5] Patent: WO2006/71958, 2006, A1. Location in patent: Page/Page column 116

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