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

HRID 1420304Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1420304
[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 2 h. 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-67e185ffc50e4ea7bfde760c38d89529
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05889178

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