(1R,2R)-trans-N-Boc-1,2-Cyclohexanediamine Chemical Properties

Melting point:

114-115℃

Boiling point:

322.1±31.0 °C(Predicted)

Density 

1.02±0.1 g/cm3(Predicted)

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

form 

powder to crystal

pka

12.26±0.40(Predicted)

color 

White to Almost white

optical activity

[α]/D -26±2°, c = 1 in chloroform

BRN 

7023564

InChI

InChI=1S/C11H22N2O2/c1-11(2,3)15-10(14)13-9-7-5-4-6-8(9)12/h8-9H,4-7,12H2,1-3H3,(H,13,14)/t8-,9-/m1/s1

InChIKey

AKVIZYGPJIWKOS-RKDXNWHRSA-N

SMILES

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

Safety Information

Hazard Codes 

C

Risk Statements 

34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 3259 8/PG 3

WGK Germany 

3

HazardClass 

8

PackingGroup 

Ⅲ

HS Code 

29242990

(1R,2R)-trans-N-Boc-1,2-Cyclohexanediamine Usage And Synthesis

Chemical Properties

White powder

Uses

(1R,2R)-trans-N-Boc-1,2-cyclohexanediamine can be used as:

• An organocatalyst in the intramolecular desymmetrization of cyclohexanones to yield 2-azabicyclo[3.3.1]nonane.
• A starting material in the synthesis of a chiral nickel catalyst applicable for the Michael addition reaction of 1,3-dicarbonyl compounds to yield nitroalkenes.

Definition

ChEBI: (1R,2R)-trans-N-Boc-1,2-cyclohexanediamine is an amine.

Synthesis

General procedure for the synthesis of (1R,2R)-N-Boc-1,2-cyclohexanediamine from di-tert-butyl dicarbonate and lev-trans-1,2-cyclohexanediamine: (R,R)-cyclohexanediamine (5.70 g, 50.0 mmol) was dissolved in 1,4-dioxane (110.0 mL). A solution of Boc-anhydride (1.09 g, 5.0 mmol) in 1,4-dioxane (35.0 mL) was slowly added dropwise with stirring at room temperature. After the dropwise addition, the reaction was continued with stirring for 5 hours. Upon completion of the reaction, the solvent was removed by rotary evaporation and the resulting residue was dissolved in water (55 mL). The insoluble material was removed by filtration and the filtrate was extracted with dichloromethane (3 x 55 mL). The organic phases were combined, washed with water, the organic layer was separated, dried with anhydrous magnesium sulfate, filtered and concentrated by rotary evaporation. Finally, purification by silica gel column chromatography afforded the yellow solid product (1R,2R)-N-Boc-1,2-cyclohexanediamine (1.00 g, 94% yield).

References

[1] Journal of the Chemical Society, Dalton Transactions, 2001, # 14, p. 2188 - 2198
[2] Patent: CN105017172, 2017, B. Location in patent: Paragraph 0043; 0044
[3] European Journal of Organic Chemistry, 2018, vol. 2018, # 1, p. 99 - 103
[4] Journal of the American Chemical Society, 2011, vol. 133, # 37, p. 14704 - 14709
[5] Organic and Biomolecular Chemistry, 2018, vol. 16, # 35, p. 6423 - 6429

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