Dry MeOH) in MeOH (1 mL), was added AcOH (0.three mL) as well as aDry

Dry MeOH) in MeOH (1 mL), was added AcOH (0.three mL) as well as a
Dry MeOH) in MeOH (1 mL), was added AcOH (0.three mL) as well as a remedy of 9 (64.0 mg, 0.1 mmol) in MeOH (1 mL). The solution was degassed and stirred below a slightly optimistic stress of hydrogen (balloon) at 23 for 16 h. The reaction was then filtered by way of a quick pad of Celite, and washed with CH2Cl2. The mixture was concentrated in vacuo and also the residue was redissolved in CH2Cl2 and was neutralized by anhydrous Na2CO3. The Bim manufacturer solvent was removed by vacuum along with the crude product was subjected to benzyl protection without further purification. Under Ar atmosphere, to a remedy of your hydrogenated crude product (0.15 mmol) in anhydrous THF was added NaH (4.8 mg, 0.four mmol). Soon after stirring for 5 min, BnBr (19 mL, 0.15 mmol) and nBu4NI (11.1 mg, 0.03 mmol) was added and the mixture was stirred at 23 for 16 h. The reaction was quenched by 1M KHSO4. The aqueous option was extracted with EtOAc (three times). The combined organic layers had been dried with MgSO4, and concentrated in vacuo. Purification from the residue by flash CXCR1 list chromatography on silica gel, eluting with 1.0 two.5 MeOHCH2Cl2 gave the desired product as a white foamy solid.(2S,3S)-1-(Benzyloxy)-4-((tert-butyldiphenylsilyl)oxy)-3-methylbutan-2-amine (syn-13) The compound was ready in line with the standard 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), 4.55 (d, J = 4.eight Hz, 2H), 3.77 three.60 (m, 3H), three.47 (dd, J = 9.3, 7.six Hz, 1H), three.18 (td, J = 7.2, three.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.three, 129.7, 128.four, 127.8, 127.7, 73.3, 72.eight, 66.8, 53.9, 38.1, 27.0, 19.2, 13.9.J Org Chem. Author manuscript; available 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 as outlined by the common hydrogenolysis and benzylation process. Purification by flash chromatography afforded anti-13 as a white foamy solid (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), 3.38 (dd, J = ten.two, 6.5 Hz, 1H), 3.26 (br, 1H), 1.83 (br, 1H), 1.51 (br, 2H), 1.08 (s, 9H), 0.92 (d, J = six.9 Hz, 3H); 13C NMR (one hundred MHz, CDCl3) 138.five, 135.6, 133.8, 133.7, 129.6, 128.4, 127.7, 127.six, 74.three, 73.two, 66.8, 29.7, 26.9, 19.3, 11.7. Relative stereochemistry determination of 9: the 13C NMR data of syn-13 matched with reported data39 and differ from that of anti-13. Therefore, the relative stereochemistry assignment was confirmed.Typical Process 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 option of 9 (1.44 g, 2.25 mmol) in MeOH (10 mL). The solution was degassed and stirred beneath a slightly good pressure of hydrogen (balloon) at 23 for 16 h. The reaction was then filtered by means of a brief pad of Celite, and washed with CH2Cl2. The mixture was concentrated in vacuo and also the residue was redissolved in CH2Cl2 and was neutralized by anhydrous Na2CO3. The solvent was removed by vacuum plus the crude item was subjected to Fmoc-protection with out further purification. To a answer in the above crude produc.