tert-Butyl N-((2S,1S)-2-hydroxycyclohexyl)carbamate
tert-Butyl N-((2S,1S)-2-hydroxycyclohexyl)carbamate Basic information
- Product Name:
- tert-Butyl N-((2S,1S)-2-hydroxycyclohexyl)carbamate
- Synonyms:
-
- tert-Butyl N-((2S,1S)-2-hydroxycyclohexyl)carbamate
- Carbamic acid, [(1S,2S)-2-hydroxycyclohexyl]-, 1,1-dimethylethyl ester (9CI)
- (1S,2S)-trans-N-Boc-2-Aminocyclohexanol
- tert-butyl (1S,2S)-2-hydroxycyclohexylcarbamate
- 2S)-2-hydroxycyclohexyl]-
- 1S,S-Boc-2-aMinocyclohexanol
- CarbaMic acid, N-[(1S,2S)-2-hydroxycyclohexyl]-, 1,1-diMethylethyl ester
- tert-butyl N-[(1S,2S)-2-hydroxycyclohexyl]carbamate
- CAS:
- 145166-06-9
- MF:
- C11H21NO3
- MW:
- 215.29
- Product Categories:
-
- Amino Alcohols
- Chiral Building Blocks
- Organic Building Blocks
- API intermediates
- Mol File:
- 145166-06-9.mol
tert-Butyl N-((2S,1S)-2-hydroxycyclohexyl)carbamate Chemical Properties
- Boiling point:
- 337.7±31.0 °C(Predicted)
- Density
- 1.06±0.1 g/cm3(Predicted)
- storage temp.
- Sealed in dry,2-8°C
- pka
- 12.11±0.40(Predicted)
- form
- solid
- Appearance
- White to off-white Solid
- BRN
- 5810950
- InChI
- InChI=1S/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-/m0/s1
- InChIKey
- XVROWZPERFUOCE-IUCAKERBSA-N
- SMILES
- C(OC(C)(C)C)(=O)N[C@H]1CCCC[C@@H]1O
tert-Butyl N-((2S,1S)-2-hydroxycyclohexyl)carbamate Usage And Synthesis
Synthesis
764659-69-0
121282-70-0
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
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