6-(BOC-AMINO)-HEXYL BROMIDE

6-(BOC-AMINO)-HEXYL BROMIDE is Colourless Liquid

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 10percent HCl (2 × 10mL), dried overMgSO4 and concentratedin vacuo. The reaction yield was 0.570 g (2.62mmol, 93percent) and the productwas taken onto the next step without further purification. Rf: 0.50, (silica gel, 60percent (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, 90percent). Rf: 0.57, (silicagel, 20percent (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].Step 2: Synthesis of tert-butyl (6-bromohexyl)carbamate (3’):1004001 To a stirred solution of compound 2 (1 g, 4.61 mmol) in toluene (30 mL) were added Ph3P (1.81 g, 6.91 mmol) and CBr4 (2.29 g, 6.91 mmol) at RT under inert atmosphere and stirred for 3 h. The mixture was diluted with water (50 mL) and extracted with EtOAc (3 x 60 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated in vacuo to obtain the crude. The crude was purified (silica gel; 20percent EtOAc/ hexanes) to afford compound 3 (1 g, 78percent) as colorless oil. 1H NMR (400 MHz, CDC13): (54.51 (br s, 1H), 3.40 (t, J= 6.8 Hz, 2H), 3.13-3.08 (m, 2H), 1.89-1.82 (m, 2H), 1.52-1.42 (m, 13H), 1.37-1.31 (m, 2H).6-(Boc-Amino)-Hexyl Bromide (3) Synthesis of Compound 32.3 [0283] To a mixture of 32.2 (3.8 g, 20 mmol, 1.0 eq) in DCM (20 mL) and H

An intermediate used in the synthesis of fluorescent indicators and various inhibitors

Molecular Weight:280.20
XLogP3:3.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Rotatable Bond Count:8
Exact Mass:279.08339
Monoisotopic Mass:279.08339
Topological Polar Surface Area:38.3
Heavy Atom Count:15
Complexity:178
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes