benzyl {(1S)-1-[2-(1-{[(3S,4R)-1-tert-butyl-4-(2,4-difluorophenyl)pyrrolidin-3-yl]carbonyl}piperidin-4-yl)-4,5-dimethylphenyl]propyl}carbamate → HCID 58660103, Verbindung
Reaktionsgleichung
[C:1]([N:5]1[CH2:9][C@@H:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])[C@H:7]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([C:26]3[CH:31]=[C:30]([CH3:32])[C:29]([CH3:33])=[CH:28][C:27]=3[C@@H:34]([NH:37]C(=O)OCC3C=CC=CC=3)[CH2:35][CH3:36])[CH2:22][CH2:21]2)=[O:19])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([N:5]1[CH2:9][C@@H:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][C:11]=2[F:17])[C@H:7]([C:18]([N:20]2[CH2:25][CH2:24][CH:23]([C:26]3[CH:31]=[C:30]([CH3:32])[C:29]([CH3:33])=[CH:28][C:27]=3[C@@H:34]([NH2:37])[CH2:35][CH3:36])[CH2:22][CH2:21]2)=[O:19])[CH2:6]1)([CH3:4])([CH3:3])[CH3:2]Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A mixture of amine 112 (910 mg, 1.41 mmol) and 10% Pd on carbon (91 mg of “Degussa type”), in ethanol/glacial acetic acid (1:1, 20 mL) was hydrogenated at atmospheric pressure for approximately 3 h. The resulting mixture was filtered through a short column of Celite®, eluting copiously with ethanol. The filtrate was evaporated and the residue was partitioned between DCM and saturated aqueous sodium bicarbonate. The organic layer was separated and the aqueous phase was re-extracted twice with DCM. The combined organic extracts were washed with water, brine, dried (MgSO4), filtered, and the filtrate concentrated in vacuo to afford 113 as a colorless oil which was used in the next step without further purification.