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Potassium Hydroxide → 1,1-Dimethylethyl (2S)-4-[(4-amino-3-fluorophenyl)methyl]-2-methyl-1-piperazinecarboxylate

HRID 644717
Notes
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Reaction equation

HRID 644717 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[C@@H:14]([CH3:25])[CH2:13]2)[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.NC1C=CC(CN2CCN(C(OC(C)(C)C)=O)[C@@H](C)C2)=CC=1.[OH-].[K+]>C(N(CC)CC)C>[NH2:8][C:7]1[CH:6]=[CH:5][C:4]([CH2:11][N:12]2[CH2:17][CH2:16][N:15]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[C@@H:14]([CH3:25])[CH2:13]2)=[CH:3][C:2]=1[F:1]
ParticipantsProcedureSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 14797Potassium HydroxideHCID 592621851,1-dimethylethyl (2S)-4-[(3-fluoro-4-nitrophenyl)methyl]-2-methyl-1-piperazinecarboxylateHCID 592622171,1-Dimethylethyl (2S)-4-[(4-aminophenyl)methyl]-2-methyl-1-piperazinecarboxylate

Product 1

HCID 592622441,1-Dimethylethyl (2S)-4-[(4-amino-3-fluorophenyl)methyl]-2-methyl-1-piperazinecarboxylate

Reagents, catalysts & solvents 1

HCID 8471
Triethylamine
Solvent

Procedure

The title compound was prepared from 1,1-dimethylethyl (2S)-4-[(3-fluoro-4-nitrophenyl)methyl]-2-methyl-1-piperazinecarboxylate (D62) using a method similar to that described for D2 in Description 2 although the reaction was carried out on an H-Cube™ continuous flow hydrogenator and triethylamine was used in place of solid KOH. δH (CDCl3, 400 MHz) 6.99 (1H, dd), 6.86 (1H, dd), 6.71 (1H, dd), 4.17 (1H, br.s), 3.79 (1H, d), 3.67 (2H, br.s), 3.40 (1H, d), 3.27 (1H, d), 3.09 (1H, td), 2.73 (1H, m), 2.56 (1H, m), 2.08 (1H, dd), 1.96 (1H, m), 1.45 (9H, s), 1.22 (3H, d).

Sources & evidence

ORD record
ord-49757ea1071b4ffcaf6f2ed421d7a6f7
Source dataset
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07700599B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes