Piperidine → (13S,16R)-16-Amino-13-isopropyl-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),18(22),19-trien-15-one

HRID 626630Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626630
C1C2C(OC(=O)[N:16](C)[C@@H:17]3[CH2:36][C:35]4=[CH:37][CH:38]=[C:32]([CH:33]=[CH:34]4)[O:31][CH2:30][CH:29]=[CH:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][O:22][CH2:21][C@H:20]([CH:39]([CH3:41])[CH3:40])[NH:19][C:18]3=[O:42])C3C(=CC=CC=3)C=2C=CC=1.N1CCCCC1>CO.[Pd]>[NH2:16][C@@H:17]1[CH2:36][C:35]2=[CH:34][CH:33]=[C:32]([CH:38]=[CH:37]2)[O:31][CH2:30][CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][CH2:23][O:22][CH2:21][C@H:20]([CH:39]([CH3:40])[CH3:41])[NH:19][C:18]1=[O:42]

Komponenten

5

Edukt 2

HCID 8082PiperidineHCID 867279389H-Fluoren-9-yl-methyl((13S,16R)-13-isopropyl-15-oxo-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),4,18(22),19-tetraen-16-yl)carbamate

Produkt 1

HCID 67028556(13S,16R)-16-Amino-13-isopropyl-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),18(22),19-trien-15-one

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 0.87 (1.46 mmol) of 9H-fluoren-9-yl-methyl((13S,16R)-13-isopropyl-15-oxo-2,11-dioxa-14-azabicyclo[16.2.2]docosa-1(21),4,18(22),19-tetraen-16-yl)-carbamate and 0.16 g of 10% Pd/C in 100 ml of methanol was stirred under a hydrogen atmosphere at RT. After stirring overnight and addition of 0.5 ml of piperidine, stirring was continued for 2 h, and the mixture was filtered and freed of solvent. The residue was separated by preparative HPLC. The required fractions were combined and freeze dried. 0.18 g of the title compound was obtained as trifluoroacetate.

Aufarbeitung

  1. stirringAfter stirring overnight
  2. stirringstirring
  3. filtrationthe mixture was filtered
  4. customThe residue was separated by preparative HPLC
  5. customfreeze dried

Quellen und Nachweise

ORD-Eintrag
ord-50b7a450dba449369224dfefe6a4f6a8
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309207B2

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