Reaktion #460842

Reaktionsgleichung

resultant product

3-[3(R)-[3-(tert-Butyloxycarbonyl)-2,2-dimethyl-4(S)-cyclohexylmethyl-5-(R)-oxazolidinyl]-3-[(1-imidazolyl)thionyloxy]-2(R)-isopropyl-1-oxopropyl]-4(R)-methyl-5(S)-phenyl-2-oxazolidinone

tri-n-butyltin hydride

→

desired product

Ausbeute 69.1%

3-[3-[3-(tert-Butyloxycarbonyl)-2,2-dimethyl-4(S)-cyclohexylmethyl-5(S)-oxazolidinyl]-2(R)-isopropyl-1-oxopropyl]-4(R)-methyl-5(S)-phenyl-2-oxazolidinone

Ausbeute 69.1%

Lösungsmittel

toluene

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturReflux
2. 2
   TemperaturThe resulting solution was cooled
3. 3
   Einengenconcentrated in vacuo
4. 4
   Sonstigethe residue was triturated with four 10 ml portions of acetonitrile, with gentle warming
5. 5
   WaschenThe combined acetonitrile extracts were washed with three 20 ml portions of hexane
6. 6
   Extraktionthe combined hexane phases were back-extracted with 20 ml of acetonitrile
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe crude product was purified by silica gel chromatography (hexane-ethyl acetate 9:1)

Vorschrift

The resultant product from Example 124 (129 mg, 0.185 mmol) was dissolved in 10 ml dry toluene and added slowly dropwise over 30 min to a refluxing solution of tri-n-butyltin hydride (93 μl, 100 mg, 0.346 mmol) in 15 ml dry toluene under a nitrogen atmosphere. Reflux was continued for an additional 10 h. The resulting solution was cooled, concentrated in vacuo, and the residue was triturated with four 10 ml portions of acetonitrile, with gentle warming. The combined acetonitrile extracts were washed with three 20 ml portions of hexane, then the combined hexane phases were back-extracted with 20 ml of acetonitrile. All acetonitrile phases were combined and concentrated in vacuo. The crude product was purified by silica gel chromatography (hexane-ethyl acetate 9:1) to give 73 mg (69%) of the desired product. 1H NMR (CDCl3) δ 0.90 (d,3H), 0.92 (d,3H), 0.9-1.1 (bm,3H), 1.06 (d,3H), 1.15-1.35 (bm,3H), 1.51 (bs,9H), 1.57-2.14 (several bm), 3.84 (m,1H), 3.97 (m,1H), 4.85 (dq,1H), 5.68 (d,1H), 7.3-7.46 (m,5H). Mass spectrum: (M+H)+ =571.

Quelle