Potassium Bicarbonate → tert-Butyl ((1S,3S)-3-hydroxycyclopentyl)carbamate

HRID 582533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 582533
[CH3:1][C:2]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([O:13]C=O)[CH2:9]1)([CH3:4])[CH3:3].C(=O)([O-])O.[K+]>CO.O.C(OCC)(=O)C>[CH3:4][C:2]([O:5][C:6](=[O:16])[NH:7][C@H:8]1[CH2:12][CH2:11][C@H:10]([OH:13])[CH2:9]1)([CH3:1])[CH3:3]

Komponenten

6

Edukt 2

HCID 516893Potassium BicarbonateHCID 86754023(1S,3S)-3-[(tert-Butoxycarbonyl)amino]cyclopentyl formate

Produkt 1

HCID 21637082tert-Butyl ((1S,3S)-3-hydroxycyclopentyl)carbamateAusbeute 52,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of (1S-trans)-[3-(formyloxy)cyclopentyl]carbamic acid 1,1-dimethylethyl ester (0.081 g, 0.35 mmol) in methanol (3 ml) was treated with a slurry of potassium hydrogen carbonate (0.707 g, 7.06 mmol) in water (1.5 ml) and stirred at room temperature for 2h. The mixture was then diluted with water (20 ml) and ethyl acetate (20 ml) and the aqueous phase was extracted with ethyl acetate (2×20 ml). The combined organic phase was dried (MgSO4) and evaporated to leave a solid which was purified by column chromatography on flash silica eluting with 30-40% ethyl acetate in cyclohexane to give the title compound (0.037 g) from diisopropyl ether m.p. 83-85° C., [α]D 0.0° (CHCl3 c=0.55%).

Aufarbeitung

  1. extractionthe aqueous phase was extracted with ethyl acetate (2×20 ml)
  2. dry with materialThe combined organic phase was dried (MgSO4)
  3. customevaporated
  4. customto leave a solid which
  5. customwas purified by column chromatography on flash silica eluting with 30-40% ethyl acetate in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-5c6b4d35a75f46c08faf4e9123193d33
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05925624

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