Reaktion #162104

Reaktionsgleichung

Benzyl N-[(1S,3R)-3-carbamoylcyclohexyl]carbamate

18d

benzyl N-[(1S,3R)-3-carbamoylcyclohexyl]carbamate

acetonitrile

bis(trifluoroacetoxy)iodobenzene

→

product 18e

Ausbeute 75.0%

benzyl N-[(1S,3R)-3-aminocyclohexyl]carbamate

Ausbeute 75.0%

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas then quenched with 1N HCl (100 mL)
2. 2
   SonstigeAfter evaporation of the acetonitrile
3. 3
   Waschenthe acidic aqueous solution was washed with EtOAc (2×150 mL)
4. 4
   workup.ADDITIONbasic by addition of solid KOH
5. 5
   Extraktionthe resulting emulsion was extracted with EtOAc (3×200 mL)
6. 6
   TrocknenThe combined organic layers were dried over Na2SO4
7. 7
   Einengenconcentrated in vacuo

Vorschrift

Benzyl N-[(1S,3R)-3-carbamoylcyclohexyl]carbamate, 18d, (9.1 g, 32.9 mmol) was suspended in a mixture of acetonitrile (100 mL) and water (100 mL) and treated with bis(trifluoroacetoxy)iodobenzene (15.5 g, 36.1 mmol). The suspension was allowed to stir at room temperature overnight and was then quenched with 1N HCl (100 mL). After evaporation of the acetonitrile, the acidic aqueous solution was washed with EtOAc (2×150 mL). The pH was adjusted to basic by addition of solid KOH and the resulting emulsion was extracted with EtOAc (3×200 mL). The combined organic layers were dried over Na2SO4 and concentrated in vacuo to provide product 18e (6.2 g, 75% yield).

Quelle