1,1,1-Trimethoxy-2-methylpropane → 4-(5-Isopropyl-(1,3,4) oxadiazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester

HRID 239129

Reaktionsgleichung

Reaktionsgleichung von HRID 239129
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]([NH:16][NH2:17])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CO[C:20](OC)(OC)[CH:21]([CH3:23])[CH3:22]>>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([C:14]2[O:15][C:20]([CH:21]([CH3:23])[CH3:22])=[N:17][N:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

3

Edukt 2

HCID 404951,1,1-Trimethoxy-2-methylpropaneHCID 22713165tert-Butyl 4-(hydrazinecarbonyl)piperidine-1-carboxylate

Produkt 1

HCID 706506414-(5-Isopropyl-(1,3,4) oxadiazol-2-yl)-piperidine-1-carboxylic acid tert-butyl ester

Versuchsvorschrift

25 g 4-hydrazinocarbonyl-piperidine-1-carboxylic acid tert-butyl ester was refluxed with 125 mL 1,1,1-trimethoxy-2-methyl-propane overnight. The excess of reagent was removed under vacuum and the residue was purified by chromatography on silica gel to give 16 g of the desired product. 1H NMR (400 MHz, MeOD): δ 4.08-4.04 (m, 2H, CH2), 3.20-3.13 (m, 2H, 2CH), 3.01 (br, 2H, CH2), 2.07-2.03 (m, 2H, CH2), 1.75-1.68 (m, 2H, CH2), 1.46 (s, 9H, 3CH3), 1.36 (d, J=6.8 Hz, 6H, 2CH3).

Aufarbeitung

  1. customThe excess of reagent was removed under vacuum
  2. customthe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-e8183874032d4cf8ac64016010edf32a
Quelldatensatz
uspto-grants-2014_02
Patentnummer
US08642774B2

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