Category: 75178-90-4

Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 75178-90-4, name is tert-Butyl (5-hydroxypentyl)carbamate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C10H21NO3

General procedure: To a stirred solution of tert-butyl 5-hydroxypentyl-carbamate(500 mg, 2.46 mmol) and TEA (498 mg, 4.92 mmol) in 5mL DCMat -10 C was added MsCl (338 mg, 2.95 mmol) dropwise and thesolution was stirred at the same temperature for 5 h. The reactionwas then quenched with water. The organic layer was washed withwater, brine, dried over MgSO4, filtered and evaporated underreduced pressure to give the desired product as yellow oil (552 mg,80%, Rf 0.5 (EtOAc)) The mesylatewas used in the next step withoutany further purification. Under N2 atmosphere 5-(tert-butoxycarbonylamino)pentyl methanesulfonate (350 mg, 1.2 mmol) wasdissolved in 5mL THF followed by the addition of LiBr (313 mg,3.6 mmol) to the solution. The reaction mixture was stirred for 16 hunder reflux, then THF was removed under vacuum. The mixturewas diluted with 10 mL water and it was extracted with DCM(3 x 10 mL). The combined organic phase was washed with water(3 x 10 mL) and brine (3 x 10 mL), dried over MgSO4 and evaporatedin vacuo. The product was purified by column chromatographyon silica gel 60 (n-hexane-EtOAc 9:1) to give whitecrystalline product (230 mg, 72%).

According to the analysis of related databases, 75178-90-4, the application of this compound in the production field has become more and more popular.

Reference:
Article; Dvoracsko, Szabolcs; Keresztes, Attila; Mollica, Adriano; Stefanucci, Azzurra; Macedonio, Giorgia; Pieretti, Stefano; Zador, Ferenc; Walter, Fruzsina R.; Deli, Maria A.; Kekesi, Gabriella; Banki, Laszlo; Tuboly, Gabor; Horvath, Gyoengyi; Toemboely, Csaba; European Journal of Medicinal Chemistry; vol. 178; (2019); p. 571 – 588;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics

Reference of 75178-90-4,Some common heterocyclic compound, 75178-90-4, name is tert-Butyl (5-hydroxypentyl)carbamate, molecular formula is C10H21NO3, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a stirred mixture of tert-butyl 5-hydroxypentylcarbamate (2)(9.8 g, 48.2 mmol) and triethyl amine (13.44 mL, 96.0 mmol) in DCM (85 mL) at-10 oC was added methanesulfonyl chloride (4.5 mL, 57.9 mmol) in adropwise fashion and the resulting solution was stirred at the same temperaturefor 3h. The reaction was quenched with the addition of water (5 mL). Theorganic phase was washed with water, brine, dried over MgSO4,filtered and evaporated under reduced pressure to afford the title compound asyellow oil (13.16g, 97%). The product was directly taken to next step withoutany further purification. 1H NMR(CDCl3) d 4.22 (t, 2H, J = 6.42 Hz), 3.09 (m, 2H), 1.82 (m, 4H), 1.56-1.40(m, 11H). 13C NMR (75 MHz, CDCl3) d 155.8, 79.3, 70.0,41.8, 37.9, 29.8, 28.3, 22.5. IR: 2981, 1707, 1516, 1354, 1171 cm-1. MS m/z (ESI) 304.26 (M +Na+).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route tert-Butyl (5-hydroxypentyl)carbamate, its application will become more common.

Reference:
Article; Maharvi, Ghulam M.; Bharucha, Adil E.; Fauq, Abdul H.; Bioorganic and Medicinal Chemistry Letters; vol. 23; 9; (2013); p. 2808 – 2811;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics