Reaktion #569280

Reaktionsgleichung

N-tert-butoxycarbonyl-4-piperidinemethanol

2-chlorobenzenesulfonic acid 3-hydroxy-5-carbomethoxyphenyl ester

triphenylphosphine

diethyl azodicarboxylate

→

material

2-Chlorobenzenesulfonic acid 3-[[1-N-(tert-butoxycarbonyl)piperidin-4-yl]methoxy]-5-carbomethoxyphenyl ester

Lösungsmittel

tetrahydrofuran

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe solvent was evaporated
2. 2
   workup.ADDITIONtreated with ether/hexane
3. 3
   Sonstigeto produce a crystalline material, which
4. 4
   Sonstigewas separated by filtration
5. 5
   SonstigeThe filtrate was evaporated to an oil
6. 6
   Wascheneluted with 20% ethyl acetate/hexane
7. 7
   SonstigeThe appropriate fractions were evaporated

Vorschrift

A solution of triphenylphosphine (0.249 g, 0.95 mol) in tetrahydrofuran (20 mL) was treated with diethyl azodicarboxylate (0.131 mL, 0.83 mol) and allowed to stir at ambient temperature for 15 min. before the addition of 2-chlorobenzenesulfonic acid 3-hydroxy-5-carbomethoxyphenyl ester (0.25 g, 0.73 mol), as prepared in the preceding step, in tetrahydrofuran (5 mL) and N-tert-butoxycarbonyl-4-piperidinemethanol (0.165 g, 0.77 mol), as prepared in step f of Example 1. The reaction mixture was allowed to stir at ambient temperature overnight. The solvent was evaporated and treated with ether/hexane to produce a crystalline material, which was separated by filtration. The filtrate was evaporated to an oil, placed on a silica gel column, and eluted with 20% ethyl acetate/hexane. The appropriate fractions were evaporated to give 0.14 g of material. 1H-NMR (CDCl3 ; 300 MHz): δ 1.25 (m, 3H), 1.47 (s, 9H), 1.78 (m, 2H), 2.74 (t, 2H), 3.77 (d, 2H), 3.88 (s, 3H), 4.12 (m, 2H), 6.90 (t, 1H), 7.38 (m, 3H), 7.62 (m, 2H), 7.97 (m, 1H).

Quelle