ChemicalBook CAS DataBase List TERT-BUTYL (3-IODOPROPYL)CARBAMATE

TERT-BUTYL (3-IODOPROPYL)CARBAMATE synthesis

5synthesis methods

Product Name:TERT-BUTYL (3-IODOPROPYL)CARBAMATE
CAS Number:167479-01-8
Molecular formula:C8H16INO2
Molecular Weight:285.12

58885-58-8

167479-01-8

General procedure for the synthesis of tert-butyl (3-iodopropyl) carbamate from tert-butyl N-(3-hydroxypropyl) carbamate: firstly, 3-amino-1-propanol (3.22 mL, 40 mmol) was dissolved in 50 mL of dichloromethane (CH2Cl2), triethylamine (Et3N, 5.6 mL, 40 mmol) was added, and stirred for 30 min. Subsequently, a solution of pre-dissolved di-tert-butyl dicarbonate (Boc2O, 9.6 g, 44 mmol) in 50 mL of CH2Cl2 was slowly added and the reaction mixture was stirred at room temperature for 14 hours. After completion of the reaction, saturated aqueous ammonium chloride solution (30 mL) was added and the mixture was extracted with CH2Cl2 (3 x 20 mL). The organic phases were combined, dried and concentrated to give the crude product (6.00 g, 86% yield), which was used directly in the next step of the reaction. Next, 1H-imidazole (1.4 g, 20.57 mmol) and triphenylphosphine (5.39 g, 20.57 mmol) were dissolved in 100 mL of CH2Cl2 and cooled to 0 °C before adding iodine (I2, 5.22 g, 20.57 mmol) in small portions. Then, a solution of the crude product (3.0 g, 17.14 mmol) obtained in the previous step dissolved in 20 mL CH2Cl2 was added. The reaction mixture was stirred for 3 h at room temperature and then poured into water (100 mL) and extracted with CH2Cl2 (50 mL). The organic phase was washed sequentially with water, 10% hydrochloric acid solution (12 mL), then extracted with CH2Cl2 (3 x 50 mL), dried and concentrated. Finally, the target product tert-butyl (3-iodopropyl)carbamate (3.78 g, 78% yield) was purified by fast chromatography (silica gel, 15% ethyl acetate/petroleum ether) as a light yellow oil.

58885-58-8
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603-35-0 Synthesis

603-35-0
735 suppliers
$5.00/5 g

791-28-6 Synthesis

791-28-6
538 suppliers
$6.00/25g

167479-01-8
51 suppliers
$65.00/250mg

Yield:-

Reaction Conditions:

with 1H-imidazole;iodine in diethyl ether;acetonitrile at 0 - 20;

Steps:

4.B
A mixture of tert-bntyl 3-hydroxypropylcarbamate (19.36 g, 110.5 mmol), triphenylphosphine (34.76 g, 132.6 mmol), imidazole (10.53 g, 154.7 mmol), diethyl ether EPO (500 mL), and acetonitrile (150 mL) was cooled to approximately 0 °C, and iodine (36.45 g, 143.6 mmol) was added in one portion. The reaction mixture was allowed to warm to room temperature slowly and stirred overnight. A precipitate formed, which was removed by filtration and washed with a small amount of diethyl ether. The filtrate was washed sequentially with water (2 x 500 mL), saturated aqueous sodium thiosulfate (2 x 250 mL), water (250 mL), and brine (250 mL); dried over magnesium sulfate; filtered; and concentrated under reduced pressure to provide a mixture of a yellow oil and a white solid. The mixture was diluted with heptane (50 mL) and filtered to remove the solid, which was washed with heptane (50 mL). The filtrate was concentrated under reduced pressure to provide an oil that was diluted with heptane (50 mL) and filtered to remove a solid, which was washed with heptane (50 mL). The filtrate was concentrated under reduced pressure to provide 22.60 g of tert~buty 3-iodopropylcarbamate as a yellow oil containing about 9 mol% triphenylphosphine oxide as determined by ¹H NMR.

References:

3M INNOVATIVE PROPERTIES COMPANY WO2006/86449, 2006, A2 Location in patent:Page/Page column 88-89

58885-58-8
193 suppliers
$10.00/1g

167479-01-8
51 suppliers
$65.00/250mg

References

83948-53-2 Synthesis