Potassium Hydroxide → 1,1-Dimethylethyl (2R)-4-[(4-aminophenyl)methyl]-2-methyl-1-piperazinecarboxylate

HRID 534721Notes

Reaction equation

HRID 534721 reaction equation
[CH3:1][C@@H:2]1[CH2:7][N:6]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([N+:15]([O-])=O)=[CH:11][CH:10]=2)[CH2:5][CH2:4][N:3]1[C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19].NC1C=CC(CN2CCN(C(OC(C)(C)C)=O)[C@@H](C)C2)=CC=1.[OH-].[K+]>>[NH2:15][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][N:6]2[CH2:5][CH2:4][N:3]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@H:2]([CH3:1])[CH2:7]2)=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 14797Potassium Hydroxide2×HCID 592621571,1-Dimethylethyl (2R)-2-methyl-4-[(4-nitrophenyl)methyl]-1-piperazinecarboxylateHCID 592622171,1-Dimethylethyl (2S)-4-[(4-aminophenyl)methyl]-2-methyl-1-piperazinecarboxylate

Product 1

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

Procedure

The title compound was prepared from 1,1-dimethylethyl (2R)-2-methyl-4-[(4-nitrophenyl)methyl]-1-piperazinecarboxylate (D4) using a method similar to that described for D2 in Description 2 although aq. 2M KOH solution was used in place of solid KOH and the reaction time was 40 minutes. MS (ES): MH+ 306.2, MNa+ 328.2.

Sources & evidence

ORD record
ord-df60df0cb3a44d13be69058840c0f323
Source dataset
uspto-grants-2014_10
Patent number
US08853218B2

Reaction notes

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