Benzene → 1-tert-Butyl 4-methyl 4-(4-chlorophenyl)piperidine-1,4-dicarboxylate

HRID 457083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 457083
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][C:11]([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)([C:14]([OH:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH:24]1C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>CO>[CH3:24][O:15][C:14]([C:11]1([C:17]2[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=2)[CH2:10][CH2:9][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:13][CH2:12]1)=[O:16]

Komponenten

5

Edukt 3

HCID 241BenzeneHCID 167693TrimethylsilyldiazomethaneHCID 248288571-(Tert-butoxycarbonyl)-4-(4-chlorophenyl)piperidine-4-carboxylic acid

Produkt 1

HCID 497602451-tert-Butyl 4-methyl 4-(4-chlorophenyl)piperidine-1,4-dicarboxylateAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a stirred 4-(4-chloro-phenyl)-piperidine-1,4-dicarboxylic acid mono-tert-butyl ester (852 mg, 2.5 mmol) in methanol (5 ml)-benzene (17.5 ml) was added 15 ml (trimethylsilyl)diazomethane (2.0 M solution in hexanes) at room temperature. The mixture was stirred for 16 hours at room temperature and concentrated in vacuo. The residual yellow oil was purified by silica gel chromatography eluting with hexane-ethyl acetate (9:1) to give the corresponding ester (780 mg, 88%).

Aufarbeitung

  1. concentrationconcentrated in vacuo
  2. customThe residual yellow oil was purified by silica gel chromatography
  3. washeluting with hexane-ethyl acetate (9:1)

Quellen und Nachweise

ORD-Eintrag
ord-4bb1cb70d67245628b89c8e81608e0fc
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186729B2

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