Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 85006-25-3, name is tert-Butyl (tert-butoxycarbonyl)oxycarbamate, A new synthetic method of this compound is introduced below., name: tert-Butyl (tert-butoxycarbonyl)oxycarbamate
Example 17: 7¾ -butyl i2-fl2-amino-3-chloro-6,7,10,ll-tetrahydro-7,ll- methano cvcloocta[bl uinolin-9-yl)ethyll (tert- butox carbonvDoxyl carbamate (HUP 16)A solution of tert-butyl-N-(tert-butoxycarbonyl)-carbamate (140 mg, 0.6 mmol) in anhydrous DMF (1.3 mL) was treated with sodium hydride (60% in oil, 26 mg, 0.65 mmol). The reaction mixture was stirred 40 min at r.t. and treated with a solution of mesylate (HUP 13) (157 mg, 0.4 mmol) in anhydrous DMF (2 mL). The reaction mixture was stirred at r.t. for 120 h, then at 60 C for 5 h. The mixture was then diluted with water (50 mL) and extracted with AcOEt (3 x 30 mL). The combined organic layers were washed with brine (50 mL), then water (50 mL), dried with Na2S04 and concentrated under reduced pressure to afford a yellow solid (313 mg). Purification by flash chromatography (AcOEt / MeOH 10/0 to 8/2, v/v) afforded the desired Huprine (HUP 16) as a white solid (98 mg, 46%).Rf (AcOEt / MeOH 8/2, v/v) = 0.50.m.p. = 114C (decomposition).1H NMR (300 MHz, CDC13): delta = 1.41 (s, 9H, N-Boc or O-Boc), 1.46 (s, 9H, N- Boc or O-Boc), 1.84-2.02 (m, 3H, Hio, ¾), 2.10-2.22 (m, 2H, Hi4), 2.52 (dd, J = 17.1 Hz, J = 3.4 Hz, 1H, ¾), 2.67-2.71 (m, 1H, H7), 2.89 (d, J = 17.5 Hz, 1H, H6), 3.06 (dd, J = 17.6 Hz, J = 5.6 Hz, 1H, H6), 3.14-3.18 (m, 1H, Hn), 3.66-3.88 (m, 2H, His), 5.03 (brs, 2H, NH2), 5.56 (d, J = 5.1 Hz, 1H, H8), 7.21 (dd, J = 9.0 Hz, J= 1.9 Hz, 1H, H2), 7.67 (d, J= 9.0 Hz, 1H, ¾), 7.77 (d, J= 1.9 Hz, 1H, H4). 13C NMR (75 MHz, CDC13): delta = 27.4 (Cn), 27.6 (N-Boc or O-Boc), 28.1 (N-Boc or O-Boc), 28.2 (C7), 28.9 (C10), 33.8 (C13), 34.8 (Ci4), 39.4 (C6), 68.1 (Ci5), 82.3 (C-Me3 of N-Boc), 84.9 (C-Me3 of O-Boc), 115.1 (Cna or Ci2a), 115.8 (Cna or Ciza), 122.0 (Ci), 124.6 (C2), 126.9 (C4), 127.0 (C8), 132.9 (C3), 134.6 (C9), 146.5 (C4a or Ci2), 147.0 (C4a or C12), 152.2 (C=0 of N-Boc), 154.8 (C=0 of O-Boc), 158.3 (C5a).MS (ESI+): m/z (%): 530.20 (100) [M+H]+, 532.20 (39).ICso rh-AC E : 14.8 +/- 3.2 nM.ICso r/i-BuChE : 421 +/- 72 nM.
The basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.
Reference:
Patent; UNIVERSITE DE ROUEN; RONCO, Cyril; RENARD, Pierre Yves; JEAN, Ludovic; NACHON, Florian; ROMIEU, Anthony; WO2011/124712; (2011); A1;,
Amide – Wikipedia,
Amide – an overview | ScienceDirect Topics