تفاعل #437742

معادلة التفاعل

(S)-2-(N-tert-butoxycarbonylamino)-1-propanol

methyl 4-hydroxy-3-nitrobenzoate

Ph3P

diisopropyl azodicarboxylate

→

methyl(S)-3-nitro-4-(2-amino-1-propoxy)benzoate

المردود 24.0%

المذيبات

THF

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةthe resulting mixture was heated
2. 2
   درجة الحرارةunder reflux overnight
3. 3
   أخرىThe solution was evaporated
4. 4
   workup.DISSOLUTIONthe residue was dissolved in CH2Cl2 (20 mL)
5. 5
   تركيزThe mixture was concentrated in vacuo
6. 6
   workup.DISSOLUTIONThe residue was dissolved in CHCl3
7. 7
   غسيلwashed with sat. NaHCO3, brine
8. 8
   تجفيفdried over Na2SO4
9. 9
   أخرىevaporated
10. 10
    أخرىThe residue was purified by column chromatography on silica-gel with 5% MeOH in CHCl3 as eluent

الإجراء التجريبي

To a stirred solution of (S)-2-(N-tert-butoxycarbonylamino)-1-propanol (0.90 g, 5.13 mmol), methyl 4-hydroxy-3-nitrobenzoate (1.01 g, 5.12 mmol), and Ph3P (1.75 g, 6.67 mmol) in THF (15 mL) was added diisopropyl azodicarboxylate (DIAD) (1.31 mL, 6.65 mmol) at room temp, and the resulting mixture was heated under reflux overnight. The solution was evaporated and the residue was dissolved in CH2Cl2 (20 mL) and TFA (10 mL). The mixture was stirred at room temp for 3 hr. The mixture was concentrated in vacuo. The residue was dissolved in CHCl3, washed with sat. NaHCO3, brine, dried over Na2SO4 and evaporated. The residue was purified by column chromatography on silica-gel with 5% MeOH in CHCl3 as eluent to give 313 mg (24%) methyl(S)-3-nitro-4-(2-amino-1-propoxy)benzoate as a pale yellow oil. 1H-NMR (CDCl3) δ 1.22 (d, 3 H, J=6.8 Hz), 3.43–3.48 (m, 1 H), 3.69–3.87 (m, 2 H), 3.89 (s, 3 H), 6.93–6.95 (m, 1 H), 7.99–8.02 (m, 1 H), 8.18–8.21 (m, 1 H).

المصدر