Uses
The propanol functionality of this versatile reagent can be introduced to many pharmaceuticals.1,2,3,4
Uses
(3-Bromopropoxy)-tert-butyldimethylsilane is a reagent in the preparation of piperidinylcarbonyl sulfamates as a novel class of antihyperlipidemic agents with LDL-receptor up-regulation via the adaptor protein autosomal recessive hypercholesterolemia.
Uses
(3-Bromopropoxy)-
tert-butyldimethylsilane may be used to introduce propanol functionality to many pharmaceuticals.
It may be used as an alkylating agent in the synthesis of the following:
- N-[2-[N-[3-(tert-butyldimethylsilyloxy)propyl]-N-ethylamino]ethyl]phthalimide
- O-(3-tert-butyldimethylsilyloxypropyl)-N-(tert-butoxycarbonyl)-L-tyrosine methyl ester
- tert-butyldimethyl-[3-(3-methyl-2-nitrophenoxy)propoxy]silane
General Description
(3-Bromopropoxy)
-tert-butyldimethylsilane is a bromo silyl ether.
Synthesis
Example C: Synthesis of 3-(3-(2,5-dioxo-4-(3,4,5-trimethoxyphenyl)-2,5-dihydro-1H-pyrrol-3-yl)-1H-indol-1-yl)-2-amino-4-methylpentanoic acid propyl ester of 3-bromopropoxy-tert-butyl dimethylsilane. (3-Bromopropoxy)tert-butyldimethylsilane was prepared using the method modified by Galka et al. (J. Lab. Comp. Rad. 2005, 48(11): 797-809). The procedure was as follows: a mixture of 3-bromo-1-propanol (39.1 mmol, 5.43 g), tert-butyldimethylchlorosilane (43.2 mmol, 6.47 g) and imidazole (46.7 mmol, 3.20 g) was stirred and reacted for 3 h at room temperature under inert gas protection. After completion of the reaction, the reaction was quenched with water and the reaction mixture was extracted with diethyl ether. The organic layers were combined, dried with anhydrous magnesium sulfate, filtered and concentrated. Purification by column chromatography (with petroleum ether as eluent) afforded the target product (3-bromopropoxy)tert-butyldimethylsilane (36.4 mmol, 93% yield). The product was characterized by 1H NMR (300 MHz, CDCl3): δ 3.73 (t, 3J = 5.7 Hz, 2H, CH2O), 3.51 (t, 3J = 6.4 Hz, 2H, CH2Br), 2.02 (q, 3J = 5.7 Hz, 3J = 6.4 Hz, 2H, CH2CH2CH2), 0.89 (s, 9H, C( CH3)3), 0.06 (s, 6H, 2×CH3).
References
[1] Heterocycles, 2004, vol. 62, p. 423 - 436
[2] Bioorganic and Medicinal Chemistry, 2009, vol. 17, # 14, p. 5080 - 5095
[3] Tetrahedron Letters, 2012, vol. 53, # 36, p. 4805 - 4808
[4] Journal of the American Chemical Society, 2012, vol. 134, # 43, p. 18101 - 18108
[5] Journal of Labelled Compounds and Radiopharmaceuticals, 2005, vol. 48, # 11, p. 797 - 809
