Reaktion #57045

Reaktionsgleichung

H-D-Glu(OtBu)-OtBu

4-carbomethoxyphenylacetaldehyde

acetic acid

NaCNBH3

→

title compound

Ausbeute 96.8%

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

Ausbeute 96.8%

Lösungsmittel

EtOAc

MeOH

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with water (50 mL), and brine (50 mL)
2. 2
   TrocknenThe organic solution was dried over sodium sulfate
3. 3
   Einengenconcentrated in vacuo
4. 4
   workup.ADDITIONThe crude oil was diluted with xylene
5. 5
   Temperaturthe solution refluxed for 5 h
6. 6
   EinengenThis solution was concentrated under reduced pressure
7. 7
   Sonstigepurified by silica gel column chromatography

Vorschrift

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).

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