Trimethylsilyldiazomethane → Methyl 4-(1-(tert-butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoate

HRID 8747

Reaktionsgleichung

Reaktionsgleichung von HRID 8747
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([CH2:18][CH2:19][CH2:20][C:21]([OH:23])=[O:22])([C:14]([O:16][CH3:17])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:24][Si](C=[N+]=[N-])(C)C>ClCCl.CO>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][C:11]([CH2:18][CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])([C:14]([O:16][CH3:17])=[O:15])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 167693TrimethylsilyldiazomethaneHCID 219839874-(1-(tert-Butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoic acid

Produkt 1

HCID 69183850Methyl 4-(1-(tert-butoxycarbonyl)-4-(methoxycarbonyl)piperidin-4-yl)butanoateAusbeute 82,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21226129Dichloromethane methanolLösungsmittel

Versuchsvorschrift

To a solution of 4-(1-(tert-butoxycarbonyl)-4-(methoxy-carbonyl)piperidin-4-yl)butanoic acid (23.4 g, 0.071 mol) from Step D in 3:1 dichloromethane/methanol (480 mL) at 0° C. was added a solution of trimethylsilyldiazomethane (53 mL, 0.11 mol, 2.0M in hexane). The reaction mixture was stirred for 15 min and then concentrated to afford 25.5 g. The residue was purified by flash chromatography eluting with 20–30% ethyl acetate in hexanes to give the title compound (20.1 g).

Aufarbeitung

  1. concentrationconcentrated
  2. customto afford 25.5 g
  3. customThe residue was purified by flash chromatography
  4. washeluting with 20–30% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-6b2aefe82fc74fb8a87e403b637a98cc
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07091211B2

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