ChemicalBook CAS DataBase List 6-(BOC-AMINO)-HEXYL BROMIDE

6-(BOC-AMINO)-HEXYL BROMIDE synthesis

13synthesis methods

Product Name:6-(BOC-AMINO)-HEXYL BROMIDE
CAS Number:142356-33-0
Molecular formula:C11H22BrNO2
Molecular Weight:280.2

75937-12-1
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$19.00/250mg

142356-33-0
152 suppliers
$13.00/100mg

Yield:142356-33-0 90%

Reaction Conditions:

with carbon tetrabromide;triphenylphosphine in dichloromethane at 0 - 20; for 2 h;Inert atmosphere;

Steps:

4.6. 1-Bromo-6-(tert-butoxycarbonylamino)-hexane (9)
To 6-aminohexan-1-ol (0.500 g, 2.82 mmol, 1 equiv.) dissolved ina 1:1 dioxane/water mixture (12 mL) was added K2CO3 (1.870 g, 13.56 mmol, 4 equiv.) and mixed at room temperature for 10 min. Ditert-butyl dicarbonate (0.7 mL, 3.39 mmol, 1.2 equiv.) was added tothe mixture and allowed to mix overnight. The reaction was dilutedwith EtOAc (12 mL) and the organic layer separated. The layer was washed with 10% HCl (2 × 10mL), dried overMgSO4 and concentratedin vacuo. The reaction yield was 0.570 g (2.62mmol, 93%) and the productwas taken onto the next step without further purification. Rf: 0.50,(silica gel, 60% (EtOAc/Hex)); 1H NMR (400 MHz, CDCl3): δ 4.51 (br s,1H), 3.61 (t, J=6.5 Hz, 2H), 3.09 (t, J=6.7 Hz, 2H), 1.42 (s, 9H), 1.55-1.30 (m, 8H) ppm; 13C NMR (100 MHz, CDCl3): δ 156.1, 79.0, 62.7, 40.4,32.6, 30.1, 28.4, 26.4, 25.3 ppm. NMR spectra are consistent with thosepreviously reported [41].To 6-(tert-butoxycarbonylamino)hexan-1-ol (0.600 g, 2.76 mmol, 1equiv.) in dry dichloromethane (14 mL) was added CBr4 (0.920 g,2.76 mmol, 1 equiv.) and PPh3 (0.720 g, 2.76 mmol, 1 equiv.) at 0 °C.The resulting mixture was allowed to warm to room temperature over2 h. The reaction was concentrated in vacuo and purified by columnchromatography to yield 0.696 g of 9 (2.48 mmol, 90%). Rf: 0.57, (silicagel, 20% (EtOAc/Hex); 1H NMR (400 MHz, CDCl3): δ 4.48 (br s), 3.66(t, J = 6.8 Hz, 2H), 3.09 (t, J = 6.5 Hz, 2H), 1.88-1.82 (m, 2H), 1.47(s, 9H), 1.54-1.18 (m, 6H) ppm; 13C NMR (100 MHz, CDCl3): δ 156.1,62.9, 51.1, 32.8, 28.5, 26.4, 25.4 ppm). NMR spectra are consistentwith those previously reported [42].

References:

Argyropoulos, Panos;Bergeret, Fabien;Pardin, Christophe;Reimer, Janice M.;Pinto, Atahualpa;Boddy, Christopher N.;Schmeing, T. Martin [Biochimica et Biophysica Acta - General Subjects,2016,vol. 1860,# 3,p. 486 - 497]

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