Réaction #40864

Équation de réaction

[(R)-1-formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester

2-methyl-2-butene

sodium chlorite

HCl

→

title compound

(R)-2-tert-Butoxycarbonylamino-4-(4-heptyloxy-phenyl)-2-methyl-butyric acid

Solvants

tert-butanol

KH2PO4

AcOEt

Conditions de réaction

Traitement

1. 1
   ExtractionThe aqueous phase is extracted twice with AcOEt
2. 2
   LavageThe combined organic layers are washed with a small amount of NaHCO3 (saturated aqueous solution)
3. 3
   Séchagedried (Na2SO4)
4. 4
   Concentrationconcentrated under reduced pressure
5. 5
   LavageColumn chromatography eluting with 5% MeOH in CH2Cl2

Mode opératoire

To a stirred solution of [(R)-1-formyl-3-(4-heptyloxy-phenyl)-1-methyl-propyl]-carbamic acid tert-butyl ester (103 mg, 0.26 mMol) in tert-butanol (1 ml) and 10% aqueous KH2PO4 (1 ml) is added 2-methyl-2-butene (0.66 ml, 5.27 mMol) and sodium chlorite (59 mg, 0.52 mMol). The mixture is stirred at RT for 1 hour. The reaction mixture is then poured onto a biphasic mixture of AcOEt and HCl (aqueous, 1M). The aqueous phase is extracted twice with AcOEt. The combined organic layers are washed with a small amount of NaHCO3 (saturated aqueous solution), dried (Na2SO4) and concentrated under reduced pressure. Column chromatography eluting with 5% MeOH in CH2Cl2 gives the title compound as a colourless oil.

Source