4-(Aminomethyl)benzonitrile → tert-butyl (2S,3R)-4-(4-cyanobenzylamino)-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate

HRID 253565

Reaktionsgleichung

Reaktionsgleichung von HRID 253565
[CH:1]1([CH2:7][C@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[C@H:9]2[CH2:11][O:10]2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:20]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH2:27])=[CH:24][CH:23]=1)#[N:21]>CC#N>[C:20]([C:22]1[CH:29]=[CH:28][C:25]([CH2:26][NH:27][CH2:11][C@@H:9]([OH:10])[C@@H:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:7][CH:1]2[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)=[CH:24][CH:23]=1)#[N:21]

Komponenten

4

Edukt 2

HCID 826084-(Aminomethyl)benzonitrileHCID 9816868erythro-N-Boc-L-cyclohexylalanine epoxide

Produkt 1

HCID 57786472tert-butyl (2S,3R)-4-(4-cyanobenzylamino)-1-cyclohexyl-3-hydroxybutan-2-ylcarbamateAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (S)-2-cyclohexyl-1-((S)-oxiran-2-yl)ethylcarbamate (67.3 mg, 0.25 mmol) in CH3CN (8 mL) was added 4-cyanobenzylamine (39.6 mg, 0.3 mmol) and the mixture was heated under reflux overnight. The solvent was removed in vacuo and the residue was purified by the preparative HPLC to give tert-butyl (2S,3R)-4-(4-cyanobenzylamino)-1-cyclohexyl-3-hydroxybutan-2-ylcarbamate (58 mg, 58%). 1H NMR: 0.82 (m, 1H), 0.95 (m, 1H), 1.10-1.48 (m, 5H), 1.45 (s, 9H), 1.55-1.68 (m, 5H), 1.76 (m, 1H), 2.65 (m, 2H), 3.46 (m, 1H), 3.85 (m, 2H), 4.49 (m, 1H), 7.42 (d, 2H), 7.59 (d, 2H). MS (E/Z): 402 (M+H+).

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. customThe solvent was removed in vacuo
  4. customthe residue was purified by the preparative HPLC

Quellen und Nachweise

ORD-Eintrag
ord-7aacd091071646e98274e8610343ad47
Quelldatensatz
uspto-grants-2011_01
Patentnummer
US07872028B2

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