tert-butyl (3R)-3-aminopiperidine-1-carboxylate → (R)-tert-butyl 3-((4-(methoxycarbonyl)-2-nitrophenyl)amino)piperidine-1-carboxylate

HRID 60070

Reaktionsgleichung

Reaktionsgleichung von HRID 60070
F[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].[NH2:15][C@@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]1>>[CH3:9][O:8][C:6]([C:5]1[CH:10]=[CH:11][C:2]([NH:15][C@@H:16]2[CH2:21][CH2:20][CH2:19][N:18]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:17]2)=[C:3]([N+:12]([O-:14])=[O:13])[CH:4]=1)=[O:7]

Komponenten

3

Edukt 2

HCID 1501974tert-butyl (3R)-3-aminopiperidine-1-carboxylateHCID 5219721Methyl 4-fluoro-3-nitrobenzoate

Produkt 1

HCID 118223843(R)-tert-butyl 3-((4-(methoxycarbonyl)-2-nitrophenyl)amino)piperidine-1-carboxylate

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

A mixture of methyl 4-fluoro-3-nitrobenzoate (1.00 g, 5.02 mmol) and (R)-tert-butyl 3-aminopiperidine-1-carboxylate (1.00 g, 5.02 mmol) were heated to 130° C. for 3 h (reaction completion monitored by TLC). The mixture was cooled to room temperature, the resulting solid was collected and washed with n-hexanes to afford (R)-tert-butyl 3-((4-(methoxycarbonyl)-2-nitrophenyl)amino)piperidine-1-carboxylate (I-21a) as a red solid. 1H-NMR (400 MHz, CDCl3): ∂ 8.89 (s, 1H), 8.40 (d, J=7.2 Hz, 1H), 8.06 (dd, J=2 and 6.8 Hz, 1H), 6.97 (d, J=8.8 Hz, 1H), 4.75 (d, J=13.6 Hz, 2H), 3.97-3.90 (m, 4H), 3.69-3.63 (m, 2H), 3.24-3.01 (m, 2H), 2.10-2.06 (m, 1H), 1.84-1.73 (m, 2H), 1.46 (s, 9H); MS calculated for C18H24N3O6 (M−H−) 378.17. found 378.4.

Aufarbeitung

  1. custom(reaction completion monitored by TLC)
  2. temperatureThe mixture was cooled to room temperature
  3. customthe resulting solid was collected
  4. washwashed with n-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-9eaa7ef004334c9f9be767263d6d5e9a
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440957B2

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