تفاعل #57045

معادلة التفاعل

H-D-Glu(OtBu)-OtBu

4-carbomethoxyphenylacetaldehyde

acetic acid

NaCNBH3

→

title compound

المردود 96.8%

tert-butyl 1-{2-[4-(methoxycarbonyl)phenyl]ethyl}-5-oxo-D-prolinate

المردود 96.8%

المذيبات

EtOAc

MeOH

ظروف التفاعل

المعالجة

1. 1
   غسيلwashed with water (50 mL), and brine (50 mL)
2. 2
   تجفيفThe organic solution was dried over sodium sulfate
3. 3
   تركيزconcentrated in vacuo
4. 4
   workup.ADDITIONThe crude oil was diluted with xylene
5. 5
   درجة الحرارةthe solution refluxed for 5 h
6. 6
   تركيزThis solution was concentrated under reduced pressure
7. 7
   أخرىpurified by silica gel column chromatography

الإجراء التجريبي

To a solution of H-D-Glu(OtBu)-OtBu (0.5 g, 2.23 mmol) in MeOH (15 mL) were added 4-carbomethoxyphenylacetaldehyde (obtained from methyl 4-formyl benzoate as described in J. Med. Chem. 1989, 32, 1277-1283) (0.4 g, 2.23 mmol), acetic acid (0.15 mL, 2.67 mmol), and NaCNBH3 (3.3 mL, 1.0 M THF solution, 3.3 mmol). The resulting solution was stirred at RT for 3 h then was diluted with EtOAc (100 mL) and washed with water (50 mL), and brine (50 mL). The organic solution was dried over sodium sulfate and concentrated in vacuo. The crude oil was diluted with xylene and the solution refluxed for 5 h. This solution was concentrated under reduced pressure and purified by silica gel column chromatography using EtOAc/hexane as eluent to afford the title compound (0.75 g, 75%) as a white solid. Rf0.45 (EtOAc/hexane 1/1); 1H NMR (CDCl3) δ 1.47 (s, 9H), 1.95-2.05 (m, 1H), 2.10-2.20 (m, 1H), 2.25-2.35 (m, 1H), 2.40-2.50 (m, 1H), 2.80-3.00 (m, 2H), 3.10-3.20 (m, 1H), 3.82 (dd, 1H), 3.91 (s, 3H), 3.90-4.01 (m, 1H), 7.25 (d, 2H), 7.96 (d, 2H).

المصدر