97538-67-5 (3R,7aS)-3-(三氯甲基)四氢吡咯并[1,2-c]恶唑-1(3H)-酮

运输方式为冰袋运输。危险性质：非危险化学品。WGK Germany:3。海关编码:29349990。

对映体纯C-和N-保护α-烷基脯氨酸的有用前体

化学合成

路线1：

• 步骤：室温下，将22ml（225mmol，2.5当量）氯醛加入到10.470g（90.94mmol，1.0当量）L-脯氨酸在45ml乙腈中的悬浮液中，搅拌19.5h；减压除去溶剂，残余物溶解于100ml DCM，过滤，重复溶解-过滤-浓缩三次，得18.141g（74.20mmol，82%）产物。
• 条件：20℃；19.50h；乙腈溶剂
• 收率：82%
• 产物：白色固体，分子式C7H8Cl3NO2，分子量244.50g·mol⁻¹，[α]20D=+34.3°（c=0.970，苯），熔点109.6℃，1H-NMR（400MHz, CDCl3）：δ=1.78-1.64(m,1H,H4'),1.96-1.85(m,1H,H4),2.13-2.02(m,1H,H3'),2.26-2.13(m,1H,H3),3.15-3.06(m,1H,H5'),3.39(ddd,J=10.9,7.8,6.0Hz,1H,H5),4.09(dd,J=8.9,4.6Hz,1H,H2),5.14(s,1H,H7)；13C-NMR(100MHz,CDCl3)：δ=25.32(t,C4),29.91(t,C3),57.87(t,C5),62.38(t,C2),100.62(s,C8),103.60(d,C7),175.43(s,C6)；IR(FT-ATR)：2958(m),2920(w),2893(w),2866(w),1784(s),1725(m),1449(w),1373(w),1359(w),1322(m),1283(m),1270(m),1243(m),1174(s),1107(s),1083(m),1043(w),1001(s),958(s),913(w),898(m),838(s),813(s),790(s),744(s)
• 参考文献：[1]Tetrahedron Asymmetry,2002,13,2229-2234；[2]Synlett,2007,18,2882-2884；[3]US2015/18269,2015,A1；[4]Chemistry-A European Journal,2015,21,23,8464-8470；[5]Journal of Heterocyclic Chemistry,1989,26,837-841；[6]WO2007/129119,2007,A1；[7]WO2015/52264,2015,A1；[8]Tetrahedron,2009,65,44,9015-9020；[9]Synlett,1999,1,33-36；[10]Journal of Organic Chemistry,2006,71,1,97-102；[11]Journal of Chemical Research,2011,35,3,167-168

路线2：