Lithium Hexamethyldisilazide → Methyl(1R,4S)-4-[(tert-Butoxycarbonyl)amino]-1-[(3R)-tetrahydrofuran-3-yl]cyclopent-2-ene-1-carboxylate

HRID 1261700Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1261700
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].I[C@@H:29]1[CH2:33][CH2:32][O:31][CH2:30]1>O1CCCC1>[C:11]([O:15][C:16]([NH:18][C@H:19]1[CH2:23][C@@:22]([C@H:29]2[CH2:33][CH2:32][O:31][CH2:30]2)([C:24]([O:26][CH3:27])=[O:25])[CH:21]=[CH:20]1)=[O:17])([CH3:14])([CH3:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 2733832Lithium HexamethyldisilazideHCID 10610130(1R,4S)-methyl 4-(tert-butoxycarbonylamino)cyclopent-2-enecarboxylateHCID 51675149(R)-3-Iodotetrahydrofuran

Produkt 1

HCID 68930507Methyl(1R,4S)-4-[(tert-Butoxycarbonyl)amino]-1-[(3R)-tetrahydrofuran-3-yl]cyclopent-2-ene-1-carboxylateAusbeute 32,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel3×

Reaktionsbedingungen

Temperatur
-78 °C

Versuchsvorschrift

To a 1.00 M solution of lithium hexamethyldisilazide in tetrahydrofuran (34.8 mL, 34.8 mmol) under N2 at −78° C. was added a solution of methyl (1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylate (4.0 g, 16 mmol) in tetrahydrofuran (20 mL). The resulting brown solution was stirred at −78° C. for 30 min before adding a solution of (3R)-3-iodotetrahydrofuran (3.75 g, 17.4 mmol) in THF (3 mL). The mixture was stirred for 10 min at −78° C. then kept in a freezer reading at −25° C. overnight. The reaction was quenched with saturated ammonium chloride, extracted with ether three times. The combined extracts were dried (MgSO4), filtered, concentrated and purified by flash column chromatography (EtOAc/Hexane) to provide the desired product (1.6 g, 31%). MS calculated for C16H25NO5: (M+H) 312.2; found 312.2.

Aufarbeitung

  1. stirringThe mixture was stirred for 10 min at −78° C.
  2. waitthen kept in a freezer reading at −25° C. overnight
  3. customThe reaction was quenched with saturated ammonium chloride
  4. extractionextracted with ether three times
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by flash column chromatography (EtOAc/Hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c5b9ebb9b5bd4374b4606c35ffc8044e
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08470827B2

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