反应 #2144503

ord-541ea795272c45f292b581b379a394f0

反应方程式

CN(C(=O)OC(C)(C)C)[C@H]1CC[C@H](C#CCCCCl)CC1
trans-[4-(5-Chloro-pent-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester
C[NH2+][C@H]1CC[C@H](C#CCCCCl)CC1.O=C([O-])C(F)(F)F
trans-[4-(5-Chloro-pent-1-ynyl)-cyclohexyl]-methyl-ammonium trifluoroacetate
→
CN[C@H]1CC[C@H](C#CCCCCl)CC1
trans-[4-(5-Chloro-pent-1-ynyl)-cyclohexyl]-methyl-amine

反应物

CN(C(=O)OC(C)(C)C)[C@H]1CC[C@H](C#CCCCCl)CC1
trans-[4-(5-Chloro-pent-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester
C[NH2+][C@H]1CC[C@H](C#CCCCCl)CC1.O=C([O-])C(F)(F)F
trans-[4-(5-Chloro-pent-1-ynyl)-cyclohexyl]-methyl-ammonium trifluoroacetate

试剂

无

反应条件

详细条件
See reaction.notes.procedure_details.

后处理

  1. 1
    其他The compound was purified
  2. 2
    workup.DISSOLUTIONby dissolving the salt in water
  3. 3
    洗涤washing it with Et2O (3×)
  4. 4
    萃取extracted with EtOAc (3×)

实验过程

In analogy to example 32.1, trans-[4-(5-Chloro-pent-1-ynyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester was converted to trans-[4-(5-Chloro-pent-1-ynyl)-cyclohexyl]-methyl-ammonium trifluoroacetate. The compound was purified by dissolving the salt in water, washing it with Et2O (3×). The water phase was adjusted to pH 8 (with aqueous saturated NaHCO3) and extracted with EtOAc (3×) to give trans-[4-(5-Chloro-pent-1-ynyl)-cyclohexyl]-methyl-amine, MS: 314 (MH+, 1Cl).

来源

DOI: 10.6084/m9.figshare.5104873.v1专利: US07335687B2uspto-grants-2008_02