| Identification | Back Directory | [Name]
(1R,2R)-trans-N-Boc-1,2-Cyclohexanediamine | [CAS]
146504-07-6 | [Synonyms]
DACH-BOC
N-Boc-1R,2R-Cyclohexanediamine
(1R,2R)-N-Boc-1,2-cyclohexanediamine
(1R,2R)-N1-Boc-1,2-cyclohexanediamine
(1R)-trans-N-Boc-1,2-diaminocyclohexane
(1R,2R)-2-Amino-1-(Boc-amino)cyclohexane
(1R,2R)-1-AMINO-2-(BOC-AMINO)-CYCLOHEXANE
(1R,2R)-trans-N-Boc-1,2-Cyclohexanediamine
Trans (1R,2R)-1N-Boc-cyclohexane-1,2-diamine
N-tert-Butoxycarbonyl-R,R-1,2-diaminocyclohexane
tert-Butyl N-((1R,2R)-2-aminocyclohexyl)carbamate
(1R,2R)-Cyclohexane-1,2-diamine, N1-BOC protected
(1R,2R)-N-tert.-Butoxycarbonylcyclohexane-1,2-diamine
(1R,2R)-Cyclohexane-1,2-diamine, N1-BOC protected 95%
(1R,2R)-trans-N-Boc-1,2-cyclohexanediamine 146504-07-6
(1R,2R)-N1-(tert-Butoxycarbonyl)-1,2-cyclohexanediamine
(1R,2R)-(-)-N-(t-Butoxycarbonyl)-1,2-cyclohexanediamine
(1R,2R)-2-Amino-1-(tert-butoxycarbonylamino)cyclohexane
((1R,2R)-2-Aminocyclohexyl)-carbamic acid tert-butyl ester
Carbamic acid, N-[(1R,2R)-2-aminocyclohexyl]-, 1,1-dimethylethyl ester
Carbamic acid, (2-aminocyclohexyl)-, 1,1-dimethylethyl ester,(1R-trans)- | [Molecular Formula]
C11H22N2O2 | [MDL Number]
MFCD08726023 | [MOL File]
146504-07-6.mol | [Molecular Weight]
214.3 |
| Chemical Properties | Back Directory | [Melting point ]
114-115℃ | [Boiling point ]
322.1±31.0 °C(Predicted) | [density ]
1.02±0.1 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Inert atmosphere,2-8°C | [form ]
powder to crystal | [pka]
12.26±0.40(Predicted) | [color ]
White to Almost white | [Optical Rotation]
[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 |
| Hazard Information | Back Directory | [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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