125664-95-1, A common compound: 125664-95-1, name is N-Propionyl-(2R)-bornane-10,2-sultam, belongs to amides-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.
A 1 M solution of NaHMDS in THF (8.3 mL, 8.3 mmol) was added over the course of 15 min to a stirred solution of (N-propionyl)-(2R)-bornane-10,2-sultam 12 (0.20 M in THF, 41.5 mL) and TBAI (0.61 g, 1.65 mmol) at -78 C. The reaction mixture was kept at this temperature for 1 h under stirring. A solution of the allyl bromide 11 (4.98 M in HMPTA, 2.2 mL) was then added dropwise to the stirring reaction mixture. The cooling bath was replaced by an octane-liquid nitrogen bath (-50 C). The reaction mixture was stirred at -50 C for 4 h and then slowly (1 h) warmed to -25 C, quenched with water (80 mL), warmed to rt and extracted with ether (4 ¡Á 50 mL). The combined organic extracts were washed with brine, dried over MgSO4 and concentrated under reduced pressure. Compound 13 (3.58 g, 77%) was isolated by column chromatography on silica gel (petroleum ether/ethyl acetate) as a colourless viscous oil; 1H NMR (CDCl3) d 0.76 (d, J = 6.7 Hz, 3H, 6-Me), 0.89 (d, J = 6.7 Hz, 1.5H, 6-Me), 0.95 (s, 3H, CH3 in bornane), 1.04 (d, J = 5.6 Hz, 1.5H, 6-Me), 1.12 (s, 1.5H, CH3 in bornane), 1.14 (s, 1.5H, CH3 in bornane), 1.17 (t, J = 5.6 Hz, 1.5H, 2-Me), 1.19 (t, J = 5.4 Hz, 1.5H, 2-Me), 1.27-2.22 (m, 14H, 3 ¡Á CH2 in bornane, CH in bornane, CH2CH2CH2 in tetrahydropyran, 6-H), 2.39-2.50 (m, 1H, 3-H), 2.68-2.77 (m, 1H, 3-H), 3.31- 3.52 (m, 4H, CH2S, CHN in bornane, 2-H), 3.54 (d, J = 7.4 Hz, 0.5H, 5-H), 3.66 (d, J = 8.7 Hz, 0.5H, 5-H), 3.76-3.91 (m, 2H, CH2O in tetrahydropyran), 4.51 (dd, J = 3.3, 2.8 Hz, 0.5H, OCHO in tetrahydropyran), 4.56 (dd, J = 3.3, 2.8 Hz, 0.5H, OCHO in tetrahydropyran), 4.95-4.98 (m, 0.5H, C=CH2), 4.99-5.01 (m, 0.5H, C=CH2), 5.00-5.04 (m, 0.5H, C=CH2), 5.12-5.16 (m, 0.5H, C=CH2); 13C NMR (CDCl3) d 16.7, 17.2, 18.3, 19.1, 19.3, 19.4, 19.8, 19.9, 20.6 (¡Á 2), 20.8, 25.4, 25.5, 26.4, 28.8, 30.1 30.5, 30.8, 31.0, 32.8, 32.9, 35.1, 36.6, 37.1, 37.2, 38.4 (¡Á 2), 44.5, 44.6, 47.7 ( 2), 48.2, 48.4, 52.9, 53.1, 62.0, 62.9, 65.1, 65.4 ( 2), 84.7, 87.2, 94.4, 100.1, 112.4, 114.3, 144.4, 146.1, 172.6, 175.8; IR (CCl4) numax: 3086, 1701, 1649 cm-1. Anal. Calcd for C25H41NO5S: C, 64.21; H, 8.84. Found: C, 64.17; H, 8.76.
In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, N-Propionyl-(2R)-bornane-10,2-sultam, other downstream synthetic routes, hurry up and to see.
Reference:
Article; Shklyaruck, Denis; Matiushenkov, Evgenii; Tetrahedron Asymmetry; vol. 22; 13; (2011); p. 1448 – 1454;,
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