(S)-Benzyl piperidine-2-carboxylate → tert-butyl 2-[(2S)-2-[(benzyloxy)carbonyl]-1-piperidinyl]-1H-1,3-benzimidazole-1-carboxylate

HRID 412668

Reaktionsgleichung

Reaktionsgleichung von HRID 412668
Cl[C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[N:3]=1.[NH:18]1[CH2:23][CH2:22][CH2:21][CH2:20][C@H:19]1[C:24]([O:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)=[O:25]>>[CH2:27]([O:26][C:24]([C@@H:19]1[CH2:20][CH2:21][CH2:22][CH2:23][N:18]1[C:2]1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[C:5]2[CH:14]=[CH:15][CH:16]=[CH:17][C:4]=2[N:3]=1)=[O:25])[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Komponenten

3

Edukt 2

HCID 12436231(S)-Benzyl piperidine-2-carboxylateHCID 23441223tert-Butyl 2-chloro-1H-benzo[d]imidazole-1-carboxylate

Produkt 1

HCID 59063194tert-butyl 2-[(2S)-2-[(benzyloxy)carbonyl]-1-piperidinyl]-1H-1,3-benzimidazole-1-carboxylate

Versuchsvorschrift

The title compound was prepared by a similar method to Preparation 2 from tert-butyl 2-chloro-1H-1,3-benzimidazole-1-carboxylate [see Preparation 46] and benzyl (2S)-2-piperidinecarboxylate [see J.A.C.S. (1 996), 118(7), 1629-1644]. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 90:10 changing to 80:20, by volume, hexane:ethyl acetate, in 5% increments to afford tert-butyl 2-[(2S)-2-[(benzyloxy)carbonyl]-1-piperidinyl]-1H-1,3-benzimidazole-1-carboxylate as an oil.

Aufarbeitung

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 90:10 changing to 80:20, by volume, hexane

Quellen und Nachweise

ORD-Eintrag
ord-bae9e8ac8db7445da45c38f603f0c930
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562964B1

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