Imidazole → 4-(Tert-butyl-dimethyl-silanyloxymethyl)-1-cycloheptyl-pyrrolidine-2-one

HRID 16200

Reaktionsgleichung

Reaktionsgleichung von HRID 16200
[BH4-].[Na+].CO[C:5]([CH:7]1[CH2:11][C:10](=O)[N:9]([CH:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[CH2:8]1)=O.[OH:20]P(O)(O)=O.N1C=CN=C1.[C:30]([Si:34](Cl)(C)C)([CH3:33])([CH3:32])[CH3:31].C([O:41][CH2:42][CH3:43])(=O)C>CO.O1CCCC1>[C:30]([SiH2:34][O:20][C:7]([CH3:8])([CH3:5])[CH:11]1[CH2:10][N:9]([CH:13]2[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)[C:42](=[O:41])[CH2:43]1)([CH3:33])([CH3:32])[CH3:31]

Komponenten

9

Edukt 6

HCID 795ImidazoleHCID 1004Phosphoric AcidHCID 8857Ethyl AcetateHCID 28928tert-Butyldimethylsilyl chlorideHCID 4311764Sodium borohydrideHCID 666569581-Cycloheptyl-5-oxo-pyrrolidine-3-carboxylic acid methyl ester

Produkt 1

HCID 1317270924-(Tert-butyl-dimethyl-silanyloxymethyl)-1-cycloheptyl-pyrrolidine-2-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Sodium borohydride (0.213 g, 5.77 mmoles) was added to a solution of Example 1A (0.7 g, 2.92 mmoles) in methanol (3 mL) and tetrahydrofuran (3 mL) and stirred at 60° C. for two hours. The reaction was cooled to 0° C. and O-phosphoric acid (1.6 g, 17.4 mmoles) was added and stirred. The reaction was filtered through a pad of celite, rinsed with methanol, and concentrated under vacuo. The crude oil was taken up in ethyl acetate (25 mL) and washed with water (25 mL). The organic layer was dried with MgSO4, filtered and evaporated in vacuo. The resulting oil was taken up in N,N-dimethylformamide (4 mL) and imidazole (391 g, 5.76 mmoles) and Tert-butyl-chloro-dimethyl-silane (583 g, 3.88 mmoles) were added and stirred for three hours. The reaction was diluted with ethyl acetate (40 mL) and washed with water (50 mL) and brine (25 mL). The organic layer was dried with MgSO4 filtered and evaporated in vacuo. The crude product was purified by flash chromatography (hexanes:ethyl acetate 95:5 to 75:25) to give the title compound as a colorless oil.

Aufarbeitung

  1. temperatureThe reaction was cooled to 0° C.
  2. stirringstirred
  3. filtrationThe reaction was filtered through a pad of celite
  4. washrinsed with methanol
  5. concentrationconcentrated under vacuo
  6. washwashed with water (25 mL)
  7. dry with materialThe organic layer was dried with MgSO4
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. stirringstirred for three hours
  11. washwashed with water (50 mL) and brine (25 mL)
  12. dry with materialThe organic layer was dried with MgSO4
  13. filtrationfiltered
  14. customevaporated in vacuo
  15. customThe crude product was purified by flash chromatography (hexanes:ethyl acetate 95:5 to 75:25)

Quellen und Nachweise

ORD-Eintrag
ord-3e971a9c509847b5957a35ece801dc74
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07737137B2

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