Electric Literature of 193751-54-1, 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. 193751-54-1, name is tert-Butyl cyclopent-3-en-1-ylcarbamate, This compound has unique chemical properties. The synthetic route is as follows.
6.63 g of mCPBA (70%) was added at 0C to a solution of 4.7 g of N-Boc-cyclopent-3-enyl amine in 80 mL of DCM. The solution obtained was stirred at rt for 1.5 h, charged with 20 mL of 20% sodium thiosulfate, stirred for 10 min, DCM was added, phases obtained were separated and the organic layer obtained was washed with saturated NaHC03 solution. The aqueous layer obtained was extracted twice with DCM, the combined organic layers obtained were dried over magnesium sulfate and solvent was evaporated. 5.2 g of the crude product was obtained which was recrystallized twice from heptane. 917 mg of syn epoxide was obtained in the form of white needles. The mother liquors obtained were subjected to chromatography (silica, toluene/EtOAc = 9: 1 – 7: 1). 3.51 g of anti epoxide in the form of a white amorphous solid was obtained.Syn epoxide: NMR (400MHz, DMSO-d6, delta, ppm, characteristic signals): 1.36 (s, 9H), 6.79 (d, 1H, J=8Hz), 1.47 (dd, 1H, J=8Hz and 14Hz), 2.17 (dd, 1H, J=8Hz and 14Hz), 3.44 (s, 2H), 3.54 (m, 1H). MS-ESI+ (m/z): 200 (M + H). TLC: toluene/EtOAc = 3:1, Rf = 0.4.Anti epoxide: 1H NMR (400MHz, DMSO-d6, delta, ppm, characteristic signals): 1.35 (s, 9H), 1.78 (d, 2H, J=15Hz), 1.98 (dd, 1H, J=8Hz and 15Hz), 3.51 (s, 2H), 3.89 (q, 1H, J=8 and 16Hz), 5.70 (d, 1H, J=8Hz). MS-ESI+ (m/z): 200 (M + H). TLC: toluene/EtOAc = 3: 1, Rf = 0.45.
The chemical industry reduces the impact on the environment during synthesis tert-Butyl cyclopent-3-en-1-ylcarbamate. I believe this compound will play a more active role in future production and life.
Reference:
Patent; NABRIVA THERAPEUTICS AG; RIEDL, Rosemarie; THIRRING, Klaus; HEILMAYER, Werner; WO2012/31307; (2012); A1;,
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