Reaktion #53864

ord-eaf61ed0328247cd8985638184dcac2d

Reaktionsgleichung

CN(C(=O)OC(C)(C)C)[C@H]1CC[C@H](C=C(Br)Br)CC1
trans-[4-(2,2-Dibromo-vinyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester
O=C(O)C(F)(F)F
TFA
→
CN[C@H]1CC[C@H](C=C(Br)Br)CC1
trans-[4-(2,2-Dibromo-vinyl)-cyclohexyl]-methyl-amine
Ausbeute 100.7%

Edukte

CN(C(=O)OC(C)(C)C)[C@H]1CC[C@H](C=C(Br)Br)CC1
trans-[4-(2,2-Dibromo-vinyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester
O=C(O)C(F)(F)F
TFA

Reagenzien

Keine

Lösungsmittel

ClCCl
CH2Cl2

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigethe reaction was evaporated
  2. 2
    workup.ADDITIONtreated with aqueous saturated NaHCO3(+Na2CO3)/Et2O (3×)
  3. 3
    Trocknendried over Na2SO4
  4. 4
    Sonstigeevaporated

Vorschrift

A solution of 975 mg (3.28 mmol) of trans-[4-(2,2-Dibromo-vinyl)-cyclohexyl]-methyl-carbamic acid tert-butyl ester in 20 ml CH2Cl2 was treated at 0° C. with 10 ml TFA (for 20 min). After 2 h at RT, the reaction was evaporated, treated with aqueous saturated NaHCO3(+Na2CO3)/Et2O (3×), dried over Na2SO4 and evaporated to yield 981 mg (87%) of trans-[4-(2,2-Dibromo-vinyl)-cyclohexyl]-methyl-amine, MS: 295 (M, 2Br).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06858651B2uspto-grants-2005_02