Reaktion #1341501

Reaktionsgleichung

Teoc-OSu

1-(3-(methylamino)-2-(tosylamino)propyl)cyclohexanol

K2CO3

→

2-(trimethylsilyl)ethyl 3-(1-hydroxycyclohexyl)-2-(tosylamino)propylmethylcarbamate

Ausbeute 74.0%

Lösungsmittel

THF H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigethe organic solvent was removed under reduced pressure
2. 2
   ExtraktionThe residue was extracted with EtOAc (2×)
3. 3
   WaschenThe combined organic phases were washed with brine
4. 4
   Sonstigedried
5. 5
   Filtrationfiltered
6. 6
   Einengenconcentrated under vacuum

Vorschrift

To a solution of 1-(3-(methylamino)-2-(tosylamino)propyl)cyclohexanol in 3:1 THF/H2O v/v (4 mL) was added K2CO3 (240 mg, 1.74 mmol), followed by Teoc-OSu (248 mg, 0.96 mmol). The resulting solution was stirred at rt for 30 min and the organic solvent was removed under reduced pressure. The residue was extracted with EtOAc (2×). The combined organic phases were washed with brine, dried, filtered and concentrated under vacuum. The residue was chromatographied on silica gel to give 2-(trimethylsilyl)ethyl 3-(1-hydroxycyclohexyl)-2-(tosylamino)propylmethylcarbamate (300 mg, 74% for two steps). MS m/z 469 (M+H+).

Quelle