4.1 Hz, 1H), two.63 (dd, J = five.0, two.eight Hz, 1H), 1.65 1.56 (m, 1H), 1.09 (s, 9H), 1.03 (d, J = 6.8 Hz, 3H); 13C NMR (100 MHz, CDCl3) 135.6, 133.6, 129.7, 127.7, 66.4, 55.1, 46.eight, 39.1, 26.eight, 19.2, 13.three. IR (CH2Cl2) n (cm-1) 3070, 2927, 2859, 2338, 1462, 1427, 1389, 1362, 1111, 933.six, 887.three, 821.7. HRMS (ESI, TOF): m/z = 347.2020, calcd For C21H28O2SiLi [M+Li]+ 347.2019.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author Manuscript(2R,3R)-4-((tert-Butyldiphenylsilyl)oxy)-2-chloro-3-methylbutan-1-ol (anti-7) The compound was ready in accordance with the typical chlorination process catalysed by (R)-5-benzyl-2,2,3,-trimethylimidazolidin-4-one trifluoroacetic acid salt. Purification by flash chromatography afforded anti-7 as colorless oil (141 mg, 75 isolated yield). 1H NMR (400 MHz, CDCl3) 7.74 7.68 (m, 4H), 7.51 7.39 (m, 6H), 4.26 four.22 (m, 1H), three.95 (dd, J = 12.two, 4.5 Hz, 1H), 3.87 (dd, J = 12.two, 6.five Hz, 1H), 3.78 (dd, J = 10.four, 5.9 Hz, 1H), 3.72 (dd, J = 10.four, four.three Hz, 1H), two.54 (br, 1H), two.27 2.16 (m, 1H), 1.ten (s, 2H), 1.06 (d, J = 7.0 Hz, 1H); 13C NMR (one hundred MHz, CDCl3) 135.six, 133.1, 129.8, 127.8, 67.four, 65.five, 65.1, 39.4, 26.9, 19.2, 14.six. IR (CH2Cl2) n (cm-1) 3383, 3071, 2932, 2859, 2361, 1470, 1427, 1389, 1111. HRMS (ESI, TOF): m/z = 377.1710, calcd For C21H30ClO2Si [M+H]+ 377.1704. The diastereoselectivity was 1.0:ten determined by 1H NMR and confirmed by Chiral HPLC (Chiralcel OD, Hex/iPrOH 99:1, 1 mL/min, 25 ), tr 11.eight min (minor diastereomer), tr 12.eight min (important diastereomer).J Org Chem. Author manuscript; offered in PMC 2014 December 06.Khumsubdee et al.PageThe solution was then converted towards the epoxide according to the standard process for preparation epoxides. Purification by flash chromatography afforded (2S,3R)-4-tertbutyldiphenylsilyloxy-1,3-epoxy-3-methylbutane (syn-10) as colorless oil (61.Losatuxizumab Cancer 3 mg, 90 isolated yield). The relative stereochemistry was determined by comparing having a known epoxide, which was reported previously.29 1H NMR (400 MHz, CDCl3) 7.74 7.66 (m, 4H), 7.48 7.38 (m, 6H), 3.75 (qd, J = 9.9, 5.1 Hz, 2H), three.02 2.99 (m, 1H), two.Dehydroaripiprazole Biological Activity 81 two.PMID:23903683 75 (m, 1H), two.57 (dd, J = five.0, 2.eight Hz, 1H), 1.68 1.60 (m, 1H), 1.10 (s, 9H), 1.03 (d, J = 7.0 Hz, 3H); 13C NMR (100 MHz, CDCl3) 135.6, 133.eight, 129.six, 127.6, 66.two, 54.0, 45.six, 38.5, 26.9, 19.three, 12.six. IR (CH2Cl2) n (cm-1) 3071, 2928, 2859, 1470, 1427, 1389, 1362, 1111, 933.six, 875.7, 821.7. HRMS (ESI, TOF): m/z = 347.2003, calcd For C21H28O2SiLi [M+Li]+ 347.2019. Relative stereochemistry determination of 7: the 1H NMR data of syn-10 matched with reported data29 and differs from that of anti-10. Thus, the relative stereochemistry assignment was confirmed.NIH-PA Author Manuscript NIH-PA Author Manuscript NIH-PA Author ManuscriptTypical Process for -Fluorination of the AldehydeA modification of reported procedure25 was utilised. 5-Benzyl-2,two,3,-trimethylimidazolidin-4one dichloroacetic acid salt (38.0 mg, 0.1 mmol) and N-fluorobenzenesulfonimide (315 mg, 1.0 mmol) was dissolved in THF (4.5 mL) and iPrOH (0.five mL). The mixture was cooled to -10 prior to addition of your aldehyde (170 mg, 0.5 mmol). The resulting mixture was stirred at – 10 for 16 h and was then warmed to 0 . For the mixture at 0 was added 1 mL MeOH and NaBH4 (200 mg, five mmol). Immediately after stirring at 0 for five minutes, the reaction was quenched by 1 M KHSO4. The mixture was diluted with water along with the aqueous remedy was extracted with EtOAc 3 occasions. The combined organic layers have been dried with MgSO4, and c.