tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylate → (3S)-tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(hydroxymethyl)piperazine-1-carboxylate

HRID 1501988

Reaktionsgleichung

Reaktionsgleichung von HRID 1501988
[F:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([CH3:10])[C:5]([CH:11]2[CH2:13][O:12]2)=[CH:4][CH:3]=1.[C:14]([N:21]1[CH2:26][CH2:25][NH:24][C@H:23]([CH2:27][OH:28])[CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15]>C(O)C>[C:8]([C:7]1[C:6]([CH3:10])=[C:5]([CH:11]([OH:12])[CH2:13][N:24]2[CH2:25][CH2:26][N:21]([C:14]([O:16][C:17]([CH3:18])([CH3:19])[CH3:20])=[O:15])[CH2:22][C@H:23]2[CH2:27][OH:28])[CH:4]=[CH:3][C:2]=1[F:1])#[N:9]

Komponenten

4

Edukt 2

HCID 24820294tert-butyl (3S)-3-(hydroxymethyl)piperazine-1-carboxylateHCID 866473076-Fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile

Produkt 1

HCID 71272768(3S)-tert-butyl 4-(2-(3-cyano-4-fluoro-2-methylphenyl)-2-hydroxyethyl)-3-(hydroxymethyl)piperazine-1-carboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

6-Fluoro-2-methyl-3-(oxiran-2-yl)benzonitrile (12.0 g, 67.7 mmol) and (S)-4-N—BOC-2-hydroxymethylpiperazine (22.0 g. 102 mmol) were suspended in ethanol (100 mL) then heated in a microwave apparatus for 30 minutes at 150° C. The reaction mixture was cooled and evaporated dryness. The residue was purified by MPLC chromatography through a 330 g Redi-sep column eluting with 5% MeOH/95% EtOAc solvent system to yield the title compound. LC-MS: M+1=394.

Aufarbeitung

  1. temperatureThe reaction mixture was cooled
  2. customevaporated dryness
  3. customThe residue was purified by MPLC chromatography through a 330 g Redi-sep column
  4. washeluting with 5% MeOH/95% EtOAc solvent system

Quellen und Nachweise

ORD-Eintrag
ord-7048003afdc641c9b6f7130ddd186f65
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206199B2

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