(R)-3-(2-Nitrophenylamino)piperidine-1-carboxylic acid tertbutyl ester → (R)-3-(2-Aminophenylamino)piperidine-1-carboxylic acid tertbutyl ester

HRID 1016549

Reaktionsgleichung

Reaktionsgleichung von HRID 1016549
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[N+:21]([O-])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][C@@H:10]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[NH2:21])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 1

HCID 59073577(R)-3-(2-Nitrophenylamino)piperidine-1-carboxylic acid tertbutyl ester

Produkt 1

HCID 59918925(R)-3-(2-Aminophenylamino)piperidine-1-carboxylic acid tertbutyl esterAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

The solution of 3(R)-(2-Nitro-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester (134 mg) and Pd-C (10%, 150 mg) in MeOH (30 ml) was stirred under H2 (1 atm) for 24 hrs. After filtration through Celite, the filtrate was concentrated to give colorless oil (96.8 mg, 80%). 1H-NMR (300 MHz, CDCl3) δ 6.80 (m, 5H), 4.10 (m, 1H), 3.78 (m, 1H), 3.39 (m, 3H), 3.15 (m, 1H), 2.95 (m, 1H), 2.08 (m, 1H), 1.80 (m, 1H), 1.60 (m 3H), 1.50 (s, 9H) ppm; LRMS (calculated for C16H21N3O2-BOC)+ 191, found (M-BOC)+ 191.

Aufarbeitung

  1. filtrationAfter filtration through Celite
  2. concentrationthe filtrate was concentrated

Quellen und Nachweise

ORD-Eintrag
ord-001da17b08b44939baa48cfa86ca7224
Quelldatensatz
uspto-grants-2002_11
Patentnummer
US06476050B2

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