Ct. The product can't be very easily converted to any known structure.Ct. The solution cannot

Ct. The product can’t be very easily converted to any known structure.
Ct. The solution cannot be easily converted to any known structure.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTypical Procedure for the -Amination of your AldehydeA modification of reported procedure38 was Bradykinin B1 Receptor (B1R) custom synthesis applied. Dibenzyl azodicarboxylate (90 , 1.29 g, three.9 mmol) and proline (70 mg, 0.6 mmol) in MeCN (ten mL) have been cooled down to -3 . The IL-3 list aldehyde (1.02 g three.0 mmol) was then added and the mixture was stirred at -3 for 2 h. The reaction was progressively warmed to 20 within ca. 1 h. The mixture was then cooled to 0 , treated with MeOH (three mL) and NaBH4 (240 mg, six.0 mmol) and was stirred for 5 min at 0 . The reaction was quenched by 1M KHSO4. The aqueous option was extracted with EtOAc 3 occasions. The combined organic layers have been dried with MgSO4, and concentrated in vacuo. Purification of the residue by flash chromatography on silica gel, eluting with 15 EtOAchexanes gave the desired alcohol as white foamy solid.J Org Chem. Author manuscript; out there in PMC 2014 December 06.Khumsubdee et al.PageNIH-PA Author ManuscriptDibenzyl 1-((2R,3S)-4-((tert-Butyldiphenylsilyl)oxy)-1-hydroxy-3-methylbutan-2yl)hydrazine-1,2-dicarboxylate (anti-9) The compound was prepared as outlined by the common -amination procedure catalysed by (R)-Proline. Purification by flash chromatography afforded anti-9 as a white foamy strong (1.54 g, 80 isolated yield). 1H NMR (400 MHz, CDCl3) 7.70 7.67 (m, 4H), 7.50 7.27 (m, 16H), six.85 (d, J = 31.1 Hz, 1H), 5.37 five.10 (m, 4H), four.45 four.12 (m, 2H), 3.80 three.41 (m, 4H), 1.95 1.66 (m, 1H), 1.12 1.09 (m, 9H), 0.99 0.88 (m, 3H); 13C NMR (100 MHz, CDCl3) 159.1, 157.four, 135.6, 133.3, 133.two, 129.6, 129.eight, 128.7, 128.6, 128.2, 127.9, 127.eight, 127.7, 68.62, 65.88, 65.56, 60.37, 35.six, 26.9, 19.3, 15.1. IR (CH2Cl2) n (cm-1) 3356, 3032, 2928, 1717, 1454, 1408, 1265, 1227, 1111, 1057. HRMS (ESI, TOF): mz = 641.3078, calcd For C37H45N2O6Si [MH] 641.3047. The diastereoselectivity was 1.0:13, determined by Chiral HPLC (Chiralcel OD, HexiPrOH 93:7, 1 mLmin, 25 ), tr ten.3 min (minor diastereomer), tr 14.four min (major diastereomer).NIH-PA Author Manuscript NIH-PA Author ManuscriptDibenzyl 1-((2S,3S)-4-((tert-Butyldiphenylsilyl)oxy)-1-hydroxy-3-methylbutan-2yl)hydrazine-1,2-dicarboxylate (syn-9) The compound was ready in accordance with the common -amidation procedure catalysed by (S)-Proline. Purification by flash chromatography afforded syn-9 as a white foamy strong (1.63 g, 85 isolated yield). 1H NMR (400 MHz, CDCl3) 7.69 7.62 (m, J = 13.five, six.six Hz, 4H), 7.50 7.24 (m, 16H), 6.96 (s, 1H), 5.30 5.22 (m, 3H), 5.13 (dd, J = 12.1, 9.6 Hz, 1H), four.36 4.16 (m, 2H), 3.86 three.70 (m, 2H), 3.59 3.44 (m, 2H), 1.80 (br, 1H), 1.11 1.08 (m, 9H), 0.93 0.90 (m, 3H); 13C NMR (100 MHz, CDCl3) 158.6, 158.2, 156.8,J Org Chem. Author manuscript; readily available in PMC 2014 December 06.Khumsubdee et al.Page156.5, 135.9, 135.six, 135.five, 135.4, 133.0, 130.1, 129.9, 128.6, 128.five, 128.1, 127.9, 127.8, 68.3, 64.0, 63.two, 60.six, 35.5, 27.0, 19.2, 14.9. IR (CH2Cl2) n (cm-1) 3356, 3032, 2959, 1724, 1470, 1408, 1261, 1223, 1111, 1053. HRMS (ESI, TOF): mz = 641.3063 calcd For C37H45N2O6Si [MH] 641.3047. The diastereoselectivity was 62:1.0, determined by Chiral HPLC (Chiralcel OD, HexiPrOH 93:7, 1 mLmin, 25 ), tr ten.two min (minor diastereomer), tr 14.3 min (key diastereomer).NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTypical Process for the Hydrogenolysis and Benzylation in the AlcoholTo Raney ickel ( 0.three g, prewashed with.