Ammonium Chloride → Ethyl 2-ethyl-4-hydroxycyclopentanecarboxylate

HRID 1969604Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1969604
[CH2:1]([CH:3]1[CH2:7][C:6](=[O:8])[CH2:5][CH:4]1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2].[BH4-].[Na+].[NH4+].[Cl-]>CO>[CH2:1]([CH:3]1[CH2:7][CH:6]([OH:8])[CH2:5][CH:4]1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2].[CH2:1]([C@@H:3]1[CH2:7][C@H:6]([OH:8])[CH2:5][C@@H:4]1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2].[CH2:1]([C@H:3]1[CH2:7][C@@H:6]([OH:8])[CH2:5][C@H:4]1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH3:2]

Komponenten

7

Edukt 3

HCID 25517Ammonium ChlorideHCID 4311764Sodium borohydrideHCID 58010012Cyclopentanecarboxylic acid, 2-ethyl-4-oxo-, ethyl ester

Produkt 3

HCID 58557073Ethyl 2-ethyl-4-hydroxycyclopentanecarboxylateHCID 58557647HCID 58557647, VerbindungHCID 86660437(1R,2S,4R)-ethyl 2-ethyl-4-hydroxycyclopentanecarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To ethyl 2-ethyl-4-oxocyclopentanecarboxylate (10 g, 54.3 mmol, Example #8, Step G) in MeOH (143 mL) was added NaBH4 (2.57 g, 67.8 mmol) portionwise. The resulting suspension was stirred for about 16 h at ambient temperature then saturated aqueous NH4Cl (240 mL) was added. The reaction mixture was stirred for about 20 min then the solution was partitioned with Et2O (300 mL). The organic layer was separated and the aqueous layer was washed with Et2O (2×150 mL). The combined organic layers were washed with brine (100 mL), dried over anhydrous MgSO4, filtered, and concd under reduced pressure. The product was purified by silica gel chromatography (220 g) eluting with a gradient of 30-70% EtOAc in heptane to give ethyl 2-ethyl-4-hydroxycyclopentanecarboxylate (8.51 g, 84%, predominantly (1S,2R,4S)-ethyl 2-ethyl-4-hydroxycyclopentanecarboxylate and (1R,2S,4R)-ethyl 2-ethyl-4-hydroxycyclopentanecarboxylate) as a clear oil: LC/MS (Table 1, Method b) Rt=2.02 min; MS m/z: 187 (M+H)+.

Aufarbeitung

  1. stirringThe reaction mixture was stirred for about 20 min
  2. customthe solution was partitioned with Et2O (300 mL)
  3. customThe organic layer was separated
  4. washthe aqueous layer was washed with Et2O (2×150 mL)
  5. washThe combined organic layers were washed with brine (100 mL)
  6. dry with materialdried over anhydrous MgSO4
  7. filtrationfiltered
  8. customThe product was purified by silica gel chromatography (220 g)
  9. washeluting with a gradient of 30-70% EtOAc in heptane

Quellen und Nachweise

ORD-Eintrag
ord-1fbb7d98332e4e67aa121a664fc5859f
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08426411B2

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