Tetrahydrofuran → 3-Cyclohexylpropyl-(ethyl)carbamate

HRID 451766

Reaktionsgleichung

Reaktionsgleichung von HRID 451766
[CH:1]1([CH2:7][C@H:8](NC(=O)OC(C)(C)C)[CH2:9]NCC)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(O[N:31]1[C:36](=[O:37])C[CH2:34][C:32]1=O)(OCC[Si](C)(C)C)=O.C1C[O:41]CC1>>[CH:1]1([CH2:7][CH2:8][CH2:9][O:41][C:36](=[O:37])[NH:31][CH2:32][CH3:34])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Komponenten

4

Edukt 3

HCID 8028TetrahydrofuranHCID 50183862,5-Dioxopyrrolidin-1-yl 2-(trimethylsilyl)ethyl carbonateHCID 59201304(S)-tert-butyl 1-cyclohexyl-3-(ethylamino)propan-2-ylcarbamate

Produkt 1

HCID 1317307163-Cyclohexylpropyl-(ethyl)carbamateAusbeute 45 %

Versuchsvorschrift

To a solution of (S)-tert-butyl 1-cyclohexyl-3-(ethylamino)propan-2-ylcarbamate (338 mg) and TeocOSu (386 mg, 1.49 mmol) in THF was added TEA (0.6 mL). The resulting solution was stirred at rt for 30 min and evaporated. The residue was purified through chromatography on silica gel to give (S)-2-(trimethylsilyl)ethyl 2-(N-tert-butoxycarbonyl)amino)-3-cyclohexylpropyl-(ethyl)carbamate (287 mg, 45% over 2 steps).

Aufarbeitung

  1. customevaporated
  2. customThe residue was purified through chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e0de30f8a9114fa4950dea2fb477176d
Quelldatensatz
uspto-grants-2013_07
Patentnummer
US08487108B2

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