Dry MeOH) in MeOH (1 mL), was added AcOH (0.3 mL) in addition to aDry

Dry MeOH) in MeOH (1 mL), was added AcOH (0.3 mL) in addition to a
Dry MeOH) in MeOH (1 mL), was added AcOH (0.3 mL) along with a option of 9 (64.0 mg, 0.1 mmol) in MeOH (1 mL). The remedy was degassed and stirred beneath a slightly optimistic stress of hydrogen (balloon) at 23 for 16 h. The reaction was then filtered through a brief pad of Celite, and washed with CH2Cl2. The mixture was concentrated in vacuo plus the residue was redissolved in CH2Cl2 and was neutralized by anhydrous Na2CO3. The solvent was removed by vacuum along with the crude product was subjected to benzyl protection without further purification. Beneath Ar atmosphere, to a answer from the hydrogenated crude product (0.15 mmol) in anhydrous THF was added NaH (4.eight mg, 0.four mmol). Right after stirring for 5 min, BnBr (19 mL, 0.15 mmol) and nBu4NI (11.1 mg, 0.03 mmol) was added and also the mixture was stirred at 23 for 16 h. The reaction was quenched by 1M KHSO4. The ERα custom synthesis aqueous resolution was extracted with EtOAc (3 times). The combined organic layers were dried with MgSO4, and concentrated in vacuo. Purification of your residue by flash chromatography on silica gel, eluting with 1.0 2.5 MeOHCH2Cl2 gave the preferred item as a white foamy strong.(2S,3S)-1-(Benzyloxy)-4-((tert-butyldiphenylsilyl)oxy)-3-methylbutan-2-amine (syn-13) The compound was prepared according to the typical hydrogenolysis and benzylation procedure. Purification by flash chromatography afforded syn-13 as a white foamy strong (22.two mg, 50 yield in two methods). 1H NMR (400 MHz, CDCl3) 7.71 7.65 (m, 4H), 7.48 7.28 (m, 11H), four.55 (d, J = four.eight Hz, 2H), 3.77 3.60 (m, 3H), 3.47 (dd, J = 9.3, 7.6 Hz, 1H), three.18 (td, J = 7.two, 3.four Hz, 1H), 2.80 (br, 2H), 1.90 1.79 (m, 1H), 1.08 (s, 9H), 0.94 (d, J = 7.0 Hz, 3H); 13C NMR (100 MHz, CDCl3) 138.1, 135.six, 133.4, 133.3, 129.7, 128.4, 127.eight, 127.7, 73.3, 72.eight, 66.eight, 53.9, 38.1, 27.0, 19.2, 13.9.J Org Chem. Author manuscript; obtainable in PMC 2014 December 06.Khumsubdee et al.PageNIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author Manuscript(2R,3S)-1-(Benzyloxy)-4-((tert-butyldiphenylsilyl)oxy)-3-methylbutan-2-amine (anti-13) The compound was ready according to the HDAC4 Species common hydrogenolysis and benzylation procedure. Purification by flash chromatography afforded anti-13 as a white foamy strong (22.three mg, 50 yield in two actions). 1H NMR (400 MHz, CDCl3) 7.70 7.67 (m, 4H), 7.49 7.28 (m, 11H), four.54 (s, 2H), 3.68 3.58 (m, 2H), 3.56 3.49 (m, 1H), three.38 (dd, J = 10.2, six.5 Hz, 1H), three.26 (br, 1H), 1.83 (br, 1H), 1.51 (br, 2H), 1.08 (s, 9H), 0.92 (d, J = 6.9 Hz, 3H); 13C NMR (100 MHz, CDCl3) 138.5, 135.6, 133.eight, 133.7, 129.6, 128.four, 127.7, 127.six, 74.three, 73.2, 66.8, 29.7, 26.9, 19.three, 11.7. Relative stereochemistry determination of 9: the 13C NMR information of syn-13 matched with reported data39 and differ from that of anti-13. Thus, the relative stereochemistry assignment was confirmed.Typical Procedure for the Preparation of -Amino AcidTo Raney ickel ( 1.5 g, prewashed with dry MeOH) in MeOH (10 mL), was added AcOH (3 mL) in addition to a solution of 9 (1.44 g, 2.25 mmol) in MeOH (ten mL). The solution was degassed and stirred under a slightly good pressure of hydrogen (balloon) at 23 for 16 h. The reaction was then filtered through a short pad of Celite, and washed with CH2Cl2. The mixture was concentrated in vacuo as well as the residue was redissolved in CH2Cl2 and was neutralized by anhydrous Na2CO3. The solvent was removed by vacuum and the crude solution was subjected to Fmoc-protection with no further purification. To a solution in the above crude produc.