FMOC-BETA-ALANINOL synthesis
- Product Name:FMOC-BETA-ALANINOL
- CAS Number:157887-82-6
- Molecular formula:C18H19NO3
- Molecular Weight:297.35
28920-43-6
156-87-6
157887-82-6
The general procedure for the synthesis of 3-(Fmoc-amino)-1-propanol from methyl 9-fluorenyl chloroformate and 3-amino-1-propanol was as follows: 3-amino-1-propanol (300 mg, 4 mmol) was dissolved in anhydrous dichloromethane (15 mL) and the reaction mixture was cooled in an ice bath. A dichloromethane solution of chloroformic acid-9-fluorenylmethyl ester (528 mg, 2 mmol) was slowly added dropwise for 30 min. Subsequently, the reaction system was warmed up to room temperature and the reaction was continued with stirring for 1.5 hours. Upon completion of the reaction, the reaction mixture was washed three times with 0.5 M hydrochloric acid solution (5 mL x 3). The organic phase was washed once more with saturated saline (5 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the resulting residue was purified by rapid chromatography on silica gel (eluent: petroleum ether solution of 50% ethyl acetate) to afford the target product 3-(Fmoc-amino)-1-propanol (585 mg, 98%) as a white solid.
28920-43-6
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157887-82-6
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Yield: 99%
Reaction Conditions:
with triethylamine in 1,4-dioxane at 0 - 20; for 5 h;Inert atmosphere;
Steps:
1.3.22 Synthesis of compound 11
To 3-amino-1-propanol (13.31 mmol, 1.0 equiv.) dissolved in 1,4-dioxane (40 mL) wasadded triethylamine (13.31 mmol, 1.0 equiv.). The mixture was cooled down to 0°C in anice bath, before dropwise addition of FmocCl (13.31 mmol, 1.0 equiv.) in 1,4-dioxane (10mL). The reaction mixture was stirred at 0°C for 1 hour and then at room temperature for4 hours. The solvent was removed under reduced pressure. The product was purified onsilica gel with 0-100% EtOAc in hexanes.
References:
Guan, Jinming;Barnard, Leanne;Cresson, Jeanne;Hoegl, Annabelle;Chang, Justin H.;Strauss, Erick;Auclair, Karine [Bioorganic and Medicinal Chemistry,2018,vol. 26,# 22,p. 5896 - 5902] Location in patent:supporting information
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156-87-6
487 suppliers
$5.00/10g
157887-82-6
117 suppliers
$8.00/250mg
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156-87-6
487 suppliers
$5.00/10g
157887-82-6
117 suppliers
$8.00/250mg