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Chloromethyl ethyl ether → Methyl(1R,4S)-4-[(tert-Butoxycarbonyl)amino]-1-(ethoxymethyl)cyclopent-2-ene-1-carboxylate

HRID 1044625
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1044625
C[Si](C)(C)[N-][Si](C)(C)C.[Li+].[C:11]([O:15][C:16]([NH:18][C@H:19]1[CH2:23][C@@H:22]([C:24]([O:26][CH3:27])=[O:25])[CH:21]=[CH:20]1)=[O:17])([CH3:14])([CH3:13])[CH3:12].Cl[CH2:29][O:30][CH2:31][CH3:32]>O1CCCC1>[C:11]([O:15][C:16]([NH:18][C@H:19]1[CH2:23][C@@:22]([CH2:29][O:30][CH2:31][CH3:32])([C:24]([O:26][CH3:27])=[O:25])[CH:21]=[CH:20]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]
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Komponenten

5

Edukt 3

HCID 18523Chloromethyl ethyl etherHCID 2733832Lithium hexamethyldisilazaneHCID 10610130(1R,4S)-methyl 4-(tert-butoxycarbonylamino)cyclopent-2-enecarboxylate

Produkt 1

HCID 57938729Methyl(1R,4S)-4-[(tert-Butoxycarbonyl)amino]-1-(ethoxymethyl)cyclopent-2-ene-1-carboxylateAusbeute 662 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a 1.0 M solution of lithium hexamethyldisilazide in tetrahydrofuran (36.7 mL) was added a solution of methyl (1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylate (4.00 g, 1.66 mmol) in tetrahydrofuran (6.0 mL) at −78° C. The resulting light brown solution was stirred at −78° C. for 30 min before (chloromethoxy)ethane (1.88 g, 19.9 mol) was added in one portion. The mixture was stirred at −78° C. for 1 h and then kept in a freezer reading at −25° C. overnight. The reaction was then quenched with saturated NH4Cl (50 mL). The organic layer was separated and the aqueous layer was extracted with CH2Cl2 three times. The combined organic layers were washed with brine, dried over Na2SO4, filtered, concentrated, and purified by flash chromatography (0 to 15% EtOAC in hexanes) to provide the desired product (3.29 g, 66%) as a cis/trans (3:2) mixture based on the analysis on reverse phase HPLC. MS calculated for C15H26NO5: (M+H) 300.2; found 200.2 (M+H-Boc).

Aufarbeitung

  1. additionwas added in one portion
  2. waitkept in a freezer reading at −25° C. overnight
  3. customThe reaction was then quenched with saturated NH4Cl (50 mL)
  4. customThe organic layer was separated
  5. extractionthe aqueous layer was extracted with CH2Cl2 three times
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by flash chromatography (0 to 15% EtOAC in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-fe3cf1098a0647b287d197cad4029bd0
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08563582B2

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