(2S)-Bornane-10,2-sultam Chemical Properties

Melting point:

185-187 °C(lit.)

alpha 

33 º (c=4.9, CHCl3)

Boiling point:

324.8±25.0 °C(Predicted)

Density 

1.1469 (rough estimate)

refractive index 

31 ° (C=1, CHCl3)

storage temp. 

Sealed in dry,Room Temperature

solubility 

almost transparency in Chloroform

form 

powder to crystal

pka

11.05±0.40(Predicted)

color 

White to Almost white

optical activity

[α]20/D +32°, c = 5 in chloroform

BRN 

4675755

InChI

InChI=1S/C10H17NO2S/c1-9(2)7-3-4-10(9)6-14(12,13)11-8(10)5-7/h7-8,11H,3-6H2,1-2H3/t7-,8-,10-/m0/s1

InChIKey

DPJYJNYYDJOJNO-CFGJQEBVSA-N

SMILES

N1[C@]2([H])[C@@]3(C(C)(C)[C@]([H])(C2)CC3)CS1(=O)=O

CAS DataBase Reference

108448-77-7(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

26-36-37/39

WGK Germany 

3

HS Code 

29242990

MSDS

• Language:English Provider:SigmaAldrich
• Language:English Provider:ACROS
• Language:English Provider:ALFA

(2S)-Bornane-10,2-sultam Usage And Synthesis

Chemical Properties

white to light yellow crystal powde

Uses

(1R)-(+)-2,10-Camphorsultam has been used as a reactant in the synthesis of pyrrolidine acid analogs as potent dual PPARα/γ agonists.

Application

(2S)-Bornane-10,2-sultam is a pharmaceutical intermediate compound that can be used to synthesize sulfonamide drugs.  (2R)-Bornane-10,2-sultam can be used as a chiral auxiliary to perform intramolecular 1,3-dipolar cycloadditions to generate bridged and fused cycloadditions with complete diastereocontrol.  Reduction of fused isoxazolidines can generate 1-azaspiro[4.5]decane, which is a potential intermediate in the asymmetric synthesis of cylindrosin alkaloids^[1].

Purification Methods

The (-)-enantiomer is recrystallised from 95% EtOH and dried in a vacuum desiccator. It dissolves in dilute aqueous NaOH and can be precipitated without hydrolysis by acidifying. It forms the N-Na salt in EtOH (by addition of Na to the EtOH solution), and the salt can be methylated with MeI to give the (-)-N-Me lactam with m 80o after recrystallisation from hot H2O and has []D -59.6o (c 5, CHCl3) [Shriner et al. J Am Chem Soc 60 2794 1938]. [Oppolzer et al. Helv Chim Acta 69 1142 1986, Weismiller et al. Org Synth 69 154 1955, Beilstein 27 III/IV 1007.]

References

[1] MARK C BAGLEY; Wolfgang O. Asymmetric synthesis of 1-azaspiro[4.5]decanes via intramolecular dipolar cycloaddition of nitrones containing the bornane-10,2-sultam chiral auxiliary[J]. Tetrahedron, asymmetry, 2000. DOI:10.1016/S0957-4166(00)00205-6.

(2S)-Bornane-10,2-sultam(108448-77-7)Related Product Information

• 3-Aminobenzenesulfonamide
• N,N-Dimethylformamide
• Dacthal
• Dimethyl ether
• Dimethyl sulfoxide
• Methanesulfonamide
• Cyclopropanesulfonamide
• Dimethyl fumarate
• Sulfanilamide
• Benzenesulfonamide
• Dimethyl carbonate
• ETHANE
• Dimethyl sulfate
• Dimethyl phthalate
• Dimethyl disulfide
• p-Toluenesulfonamide
• (2R)-Bornane-10,2-sultam
• (1S)-(+)-10-CAMPHORSULFONAMIDE