Réaction #162185

Équation de réaction

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

18d

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

2,4,6-trichloro-1,3,5-triazine

→

residue

benzyl (1S,3R)-3-cyanocyclohexylcarbamate

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreAfter 1 hour a precipitate had formed
2. 2
   workup.STIRRINGStirred for an additional 3 hours
3. 3
   Autrethen quenched with ice water (100 mL)
4. 4
   Extractionextracted with CH2Cl2 (2×125 mL)
5. 5
   Lavagethen washed with 1N HCl (100 mL)
6. 6
   ConcentrationThe organic layer was concentrated in vacuo

Mode opératoire

A suspension of benzyl N-[(1S,3R)-3-carbamoylcyclohexyl]carbamate, 18d, (0.69 g, 2.50 mmol) in DMF (10 mL) at 0° C. was treated with 2,4,6-trichloro-1,3,5-triazine (0.61 g, 3.29 mmol) and allowed to stir while slowly warming to room temperature. After 20 minutes, the solution became gold in color. After 1 hour a precipitate had formed. Stirred for an additional 3 hours then quenched with ice water (100 mL) and extracted with CH2Cl2 (2×125 mL) then washed with 1N HCl (100 mL). The organic layer was concentrated in vacuo to afford an 730 mg of a residue that was purified using a pad of silica gel (45 mL) using 30% EtOAc/hexanes as eluent to afford 621 mg of a white solid after vacuum drying.

Source