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

HRID 644698Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 644698
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-e00445d832c140a6b095cc337baa19e7
Quelldatensatz
uspto-grants-2010_04
Patentnummer
US07700599B2

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