Hydrochloric Acid → Methyl(1R,2R,5S,6S)-6-fluoro-2-hydroxy-4-oxobicyclo[3.1.0]hexane-6-carboxylate

HRID 507821Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507821
[Si]([O:8][C@@H:9]1[CH2:14][C:13](=[O:15])[C@@H:12]2[C@H:10]1[C@@:11]2([F:20])[C:16]([O:18][CH3:19])=[O:17])(C(C)(C)C)(C)C.Cl>C(#N)C.CCOC(C)=O>[F:20][C@@:11]1([C:16]([O:18][CH3:19])=[O:17])[C@@H:12]2[C@H:10]1[C:9](=[O:8])[CH2:14][C@H:13]2[OH:15]

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 11587530Methyl(1R,2R,5S,6S)-2-{[tert-butyl(dimethyl)silyl]oxy}-6-fluoro-4-oxobicyclo[3.1.0]hexane-6-carboxylate

Produkt 1

HCID 11665535Methyl(1R,2R,5S,6S)-6-fluoro-2-hydroxy-4-oxobicyclo[3.1.0]hexane-6-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

TBS-ether 6′ (150 mg, 0.528 mmol) was treated with 1 M HCl (0.106 mL) in acetonitrile (0.8 mL) at rt for 2 h. The reaction was diluted with EtOAc, quenched by addition of a small amount of saturated aq. NaHCO3, washed with H2O and brine (twice), and dried over Na2SO4. The solvents were removed under reduced pressure, and the resulting residue was purified by flash silica gel column chromatography to afford hydroxy ketone 7′ as colorless solid: 1H NMR (CDCl3, 400 MHz) δ 4.60 (d, J=5.2 Hz, 1H), 3.72 (s, 3H), 2.67 (dd, J=5.2, 3.6 Hz, 1H), 2.42 (dd, J=5.2, 2.4 Hz, 1H), 2.34 (dd, J=18.9, 5.2 Hz, 1H), 2.22 (br-s, 1H), 2.08 (d, J=18.9 Hz, 1H), 1.93 (dd, J=3.6, 2.4 Hz, 1H); 13C NMR (CDCl3, 101 MHz) δ 208.8, 169.8, 68.3, 52.5, 42.7, 36.2, 34.2, 25.2.

Aufarbeitung

  1. customquenched by addition of a small amount of saturated aq. NaHCO3
  2. washwashed with H2O and brine (twice), and
  3. dry with materialdried over Na2SO4
  4. customThe solvents were removed under reduced pressure
  5. customthe resulting residue was purified by flash silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-677aea82318345e581ab3a9e29b0ee45
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786314B2

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