![](/CAS/GIF/164365-88-2.gif)
tert-butyl (4-bromobutyl)carbamate synthesis
- Product Name:tert-butyl (4-bromobutyl)carbamate
- CAS Number:164365-88-2
- Molecular formula:C9H18BrNO2
- Molecular Weight:252.15
![4-Amino-1-butanol](/CAS/GIF/13325-10-5.gif)
13325-10-5
305 suppliers
$10.00/1g
![Di-tert-butyl dicarbonate](/CAS/GIF/24424-99-5.gif)
24424-99-5
824 suppliers
$13.50/25G
![tert-butyl (4-bromobutyl)carbamate](/CAS/GIF/164365-88-2.gif)
164365-88-2
118 suppliers
$31.00/100mg
Yield:164365-88-2 80%
Reaction Conditions:
Stage #1:4-Aminobutanol;di-tert-butyl dicarbonate with triethylamine in acetonitrile at 0; for 6 h;
Stage #2: with carbon tetrabromide;triphenylphosphine in tetrahydrofuran for 3 h;
Steps:
Synthesis of tert-butyl (4-bromobutyl)carbamate (10)
To a solution of 4-amino-1-butanol (1.50 g, 16.8 mmol) in MeCN (150 mL) were added TEA (4.68 mL) and Boc2O (4.03 g, 18.5 mL) at 0 °C. The mixture was stirred for 6 h and quenched with water. The mixture was poured onto water and extracted with EtOAc three times. The combined organic layers were dried over Na2SO4 and concentrated under reduced pressure. The crude product 6 (2.68 g) was used without further purification. The crude product 6 was dissolve in THF (130 mL) followed by addition of Ph3P (7.06 g, 26.9 mmol). Then CBr4 (8.92 g, 26.9 mmol) was slowly added to the mixture. After 3 h, the solution was filtered through Celite® pad and washed with Et20. The solvents were removed under reduced pressure. The residue was purified by flash chromatography on silica (hexane:EtOAc = 3:1) to yield a colourless oil (4.38 g, 80percent).‘H NMR (500 MHz, CDC13) 4.54 (br s, 1H), 3.43 (t, J= 6.7 Hz, 2H), 3.17 (q, J= 6.7 Hz, 2H), 1.90 (dt, J= 14.8, 6.8 Hz, 2H), 1.65 (m, 2H), 1.45 (s, 9H).
References:
UNIVERSITY OF ADELAIDE;ABELL, Andrew;POLYAK, Steven;TIEU, William;BOOKER, Grant;JUN, Kwang Lee;RODRIGEZ, Beatriz Blanco WO2020/87122, 2020, A1 Location in patent:Page/Page column 26; 27
![4-(tert-ButoxycarbonylaMino)-1-butanol](/CAS/GIF/75178-87-9.gif)
75178-87-9
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$6.00/100mg
![tert-butyl (4-bromobutyl)carbamate](/CAS/GIF/164365-88-2.gif)
164365-88-2
118 suppliers
$31.00/100mg
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4509-90-4
227 suppliers
$15.00/1g
![tert-Butanol](/CAS/GIF/75-65-0.gif)
75-65-0
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$10.00/10ml
![tert-butyl (4-bromobutyl)carbamate](/CAS/GIF/164365-88-2.gif)
164365-88-2
118 suppliers
$31.00/100mg
![Di-tert-butyl dicarbonate](/CAS/GIF/24424-99-5.gif)
24424-99-5
824 suppliers
$13.50/25G
![1-ButanaMine, 4-broMo-, hydrobroMide](/CAS/GIF/24566-81-2.gif)
24566-81-2
93 suppliers
$9.00/250mg
![tert-butyl (4-bromobutyl)carbamate](/CAS/GIF/164365-88-2.gif)
164365-88-2
118 suppliers
$31.00/100mg
![4-bromobutan-1-amine](/CAS/20180808/GIF/33977-38-7.gif)
33977-38-7
11 suppliers
inquiry
![Di-tert-butyl dicarbonate](/CAS/GIF/24424-99-5.gif)
24424-99-5
824 suppliers
$13.50/25G
![tert-butyl (4-bromobutyl)carbamate](/CAS/GIF/164365-88-2.gif)
164365-88-2
118 suppliers
$31.00/100mg