Sodium borohydride → 1,1-Dimethylethyl (2R)-2-methyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylate

HRID 534722Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 534722
NC1C=CC(CN2CCN(C(OC(C)(C)C)=O)[C@H](C)C2)=CC=1.[CH3:23][C@H:24]1[CH2:29][N:28]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([NH:37][CH3:38])=[CH:33][CH:32]=2)[CH2:27][CH2:26][N:25]1[C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40].[BH4-].[Na+]>>[CH3:23][C@@H:24]1[CH2:29][N:28]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([NH:37][CH3:38])=[CH:33][CH:32]=2)[CH2:27][CH2:26][N:25]1[C:39]([O:41][C:42]([CH3:43])([CH3:45])[CH3:44])=[O:40]

Komponenten

4

Edukt 3

HCID 4311764Sodium borohydrideHCID 592621311,1-Dimethylethyl (2S)-2-methyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylateHCID 592621641,1-Dimethylethyl (2R)-4-[(4-aminophenyl)methyl]-2-methyl-1-piperazinecarboxylate

Produkt 1

HCID 592622231,1-Dimethylethyl (2R)-2-methyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylate

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

The title compound was prepared from 1,1-dimethylethyl (2R)-4-[(4-aminophenyl)methyl]-2-methyl-1-piperazinecarboxylate (D5) using a method similar to that described for D3 in Description 3A although the reaction was heated at 50° C. for 48 h prior to addition of sodium borohydride. δH (CDCl3, 400 MHz) 7.13 (2H, d), 6.57 (2H, d), 4.16 (1H, m), 3.78 (1H, d), 3.42 (1H, d), 3.29 (1H, d), 3.08 (1H, td), 2.83 (3H, s), 2.75 (1H, m), 2.59 (1H, m), 2.07 (1H, dd), 1.94 (1H, m), 1.45 (9H, s), 1.21 (3H, d). MS (ES+): 342.3 (MNa+), 220.2, no molecular ion (MH+) observed.

Quellen und Nachweise

ORD-Eintrag
ord-795347ebbaf644488f4324a270994c43
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08853218B2

Notizen zur Reaktion

Wird geladen…