Réaction #1790

Équation de réaction

N-Boc-trans-1-amino-4-cyclohexanol

diethyl azodicarboxylate

methyl 4-hydroxy-2-methoxybenzoate

triphenylphosphine

→

methyl 4-[N-Boc-cis-1-amino-4-cyclohexanoyloxy]-2-methoxybenzoate

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   FiltrationThe reaction was filtered
2. 2
   Autrethe solvent was removed under reduced pressure
3. 3
   AutreThe residue was chromatographed on a silica gel column
4. 4
   LavageEtOAc and eluted with same
5. 5
   Autrethe solvent removed under reduced pressure

Mode opératoire

To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (1.09 g, 6.0 mmol) in dry THF (7 mL) was added triphenylphosphine (1.57 g, 6.0 mmol) and the solution was cooled to 0° C. A 4.0 mL volume of N-Boc-trans-1-amino-4-cyclohexanol (1 g, 4.0 mmol) and diethyl azodicarboxylate (945 μL, 6.0 mmol) in THF was added dropwise via addition funnel over 0.5 h. The reaction was filtered and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column packed in 70:30 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-[N-Boc-cis-1-amino-4-cyclohexanoyloxy]-2-methoxybenzoate.

Source