Reaktion #1790

Reaktionsgleichung

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

Lösungsmittel

THF

THF

Reaktionsbedingungen

Aufarbeitung

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

Vorschrift

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.

Quelle