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

HRID 644698Notes

Reaction equation

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]

Participants

Reactant 3

HCID 4311764Sodium borohydride

HCID 592621311,1-Dimethylethyl (2S)-2-methyl-4-{[4-(methylamino)phenyl]methyl}-1-piperazinecarboxylate

HCID 592621641,1-Dimethylethyl (2R)-4-[(4-aminophenyl)methyl]-2-methyl-1-piperazinecarboxylate

Product 1

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

Conditions

Temperature: 50 °C

Procedure

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.

Sources & evidence

ORD record: ord-e00445d832c140a6b095cc337baa19e7
Source dataset: uspto-grants-2010_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07700599B2

Reaction notes

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