Electric Literature of 167355-41-1, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 167355-41-1, name is 6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine belongs to bromides-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.
DI-TERT-BUTYLDICARBONATE (575. 7 mg, 2. 64 mmol) in methylene chloride (5. 0 mL) is added in one portion to a solution of methylene chloride (7. 0 mL) at room temperature that contains (RAC)-6-BROMO-1, 2, 3, 4-tetrahydronaphthalen-2-ylamine (591. 6 mg, 2. 62 mmol) and triethylamine (1. 1 mL, 7. 89 MMOL). After stirring at room temperature for 19 h in air, the resulting amber solution is diluted with methylene chloride (25 mL), washed with a saturated aqueous solution of sodium chloride (2 x 50 mL), dried over magnesium sulfate, and evaporated to dryness under reduced pressure to give the title compound as a pale yellow solid. The purity of isolated 29 was >95%, as determined by 1H NMR spectroscopy, and was used without further purification. mp 107-108 C. H NMR (CDCl3) : No.1. 45 (s, 9H, C (CH3) 3), 1. 70 (m, 1H, H-3), 2. 04 (m, 1H, H-3), 2. 55 (dd, J= 16. 5 Hz, 8. 5 Hz, 1H, H-1), 2. 84 (pseudo t, J= 6. 5 Hz, 2H, H-4), 3. 05 (dd, J= 16. 5 Hz, 5. 0 Hz, 1H, H-1), 3. 94 (br, 1H, H-2), 4. 58 (br, 1H, NH), 6. 91 (d, J= 8. 0 Hz, 1H, H-8), 7. 22 (m, 2H, overlapping H-5 and H- 7). 13C NMR (CDCl3) : No.27. 1 (CH2, C-4), 28. 4 (C (CH3) 3), 28. 7 (CH2, C-3), 35. 6 (CH2, C-1), 46. 0 (CH, C-2), 79. 4 (C (CH3) 3), 119. 6 (C-Br, C-6), 128. 9 (CH, C-7), 131. 0 (CH, C-8), 131. 5 (CH, C-5), 133. 3 (C-8a), 137. 8 (C-4a), 155. 3 (NHCO2). LCMS m/z calcd. for C15H2OBRN02 ([M] +) 325 ; found 311 ([M – C4H7 + CH3CN] +, 22%), 270 ( [M-C4H7] +, 81%), 267 ( [M- C5H702 + CH3CN] +, 43%), 226 ([M-C5H702] +, 100%), 209 ([M – C5H10NO2]+, 94%).
The synthetic route of 6-Bromo-1,2,3,4-tetrahydronaphthalen-2-amine has been constantly updated, and we look forward to future research findings.
Reference:
Patent; ACHILLION PHARMACEUTICALS, INC.; WO2005/19228; (2005); A1;,
Bromide – Wikipedia,
bromide – Wiktionary