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Isopropyl iodide → Methyl(1S,4S)-4-[(tert-Butoxycarbonyl)amino]-1-isopropylcyclopent-2-ene-1-carboxylate

HRID 1261634
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1261634
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].[CH:28](I)([CH3:30])[CH3:29]>C1COCC1>[C:11]([O:15][C:16]([NH:18][C@H:19]1[CH2:23][C@@:22]([CH:28]([CH3:30])[CH3:29])([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 6362Isopropyl iodideHCID 2733832Lithium HexamethyldisilazideHCID 10610130(1R,4S)-methyl 4-(tert-butoxycarbonylamino)cyclopent-2-enecarboxylate

Produkt 1

HCID 60122269Methyl(1S,4S)-4-[(tert-Butoxycarbonyl)amino]-1-isopropylcyclopent-2-ene-1-carboxylateAusbeute 77,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To a 1.00 M solution of lithium hexamethyldisilazide in THF (202 mL) at −78° C. was added a solution of methyl (1R,4S)-4-[(tert-butoxycarbonyl)amino]cyclopent-2-ene-1-carboxylate (22.10 g, 91.59 mmol) in THF (36.2 mL) over 10 min. The solution was stirred at −78° C. for 30 min before isopropyl iodide (10.0 mL, 100 mmol) was added in one portion. The mixture was then moved to a freezer reading at −24° C. and kept overnight. The reaction was quenched with aqueous ammonium chloride and the resulting solution was extracted with ether three times. The ether layers were dried over sodium sulfate and evaporated in vacuo. The residue was purified by flash chromatography on silica eluting with 10% ethyl acetate/hexane to give the title compound (20.2 g). MS calculated for C15H25NO4: (M+H)+ 284; found 184.2 (M-Boc+H)+.

Aufarbeitung

  1. additionwas added in one portion
  2. customwas then moved to a freezer reading at −24° C.
  3. customThe reaction was quenched with aqueous ammonium chloride
  4. extractionthe resulting solution was extracted with ether three times
  5. dry with materialThe ether layers were dried over sodium sulfate
  6. customevaporated in vacuo
  7. customThe residue was purified by flash chromatography on silica eluting with 10% ethyl acetate/hexane

Quellen und Nachweise

ORD-Eintrag
ord-609dffad9a304bb1a64dd5cbb2d3f59e
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08470827B2

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