Boc-(+/-)-trans-2-aminocyclohexanol Chemical Properties

Boiling point:

337.7±31.0 °C(Predicted)

Density 

1.06±0.1 g/cm3(Predicted)

storage temp. 

2-8°C

pka

12.11±0.40(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1/C11H21NO3/c1-11(2,3)15-10(14)12-8-6-4-5-7-9(8)13/h8-9,13H,4-7H2,1-3H3,(H,12,14)/t8-,9-/s3

InChIKey

XVROWZPERFUOCE-JQEWEITDNA-N

SMILES

C(OC(C)(C)C)(=O)N[C@@H]1CCCC[C@H]1O |&1:8,13,r|

Boc-(+/-)-trans-2-aminocyclohexanol Usage And Synthesis

Uses

tert-Butyl (2-Hydroxycyclohexyl)carbamate is a reagent used in the preparation of N-aryl acetamides from the corresponding nitro compounds.

Synthesis

General procedure for the synthesis of trans-N-Boc-cyclohexylamino alcohols from the compounds (CAS: 764659-69-0): the product of part A (8.0 g, 26.2 mmol) was dissolved in a solvent mixture of cyclohexene (100 mL) and ethanol (150 mL), and palladium/carbon catalyst (2.0 g) was added. The reaction mixture was heated to reflux for 6 h. Upon completion of the reaction, the catalyst was removed by filtration through a Celite pad. The filtrate was concentrated to afford tert-butyl (1S,2S)-2-hydroxy-cyclohexyl-carbamate (5.7 g, 100% yield) as a white solid. Mass spectral analysis showed M/Z 216.2 ([M + H]+).

References

[1] Patent: WO2004/83174, 2004, A2. Location in patent: Page 172
[2] Patent: WO2005/87731, 2005, A1. Location in patent: Page/Page column 321
[3] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 16, p. 4419 - 4427
[4] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 1, p. 119 - 132

Boc-(+/-)-trans-2-aminocyclohexanol(121282-70-0)Related Product Information

• 2-N-BOC-AMINO-CYCLOHEXANOL
• BIS(N-BOC)-2-DEOXYSTREPTAMINE
• Boc-(+/-)-trans-2-aminocyclohexanol