Benzylamine → tert-butyl (3aR,7aS)-2-(benzylamino)-3a,4,5,6,7,7a-hexahydrobenzimidazole-1-carboxylate

HRID 2053539Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2053539
CS[C:3]1[N:7]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[C@H:6]2[CH2:15][CH2:16][CH2:17][CH2:18][C@H:5]2[N:4]=1.[CH2:19]([NH2:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[C:11]([O:10][C:8]([N:7]1[C@H:6]2[CH2:15][CH2:16][CH2:17][CH2:18][C@H:5]2[N:4]=[C:3]1[NH:26][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Komponenten

4

Edukt 2

HCID 7504BenzylamineHCID 86596330cis-3a,4,5,6,7,7a-Hexahydro-2-methylthio-benzimidazole-1-carboxylic Acid, Tert-Butyl Ester

Produkt 1

HCID 68569663tert-butyl (3aR,7aS)-2-(benzylamino)-3a,4,5,6,7,7a-hexahydrobenzimidazole-1-carboxylateAusbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of intermediate 76 (200 mg, 0.0.740 mmol), benzylamine (0.5 mL, 4.6 mmol) is heated at 100° C. (reaction block) overnight. The reaction mixture is cooled to RT. The reaction mixture is diluted with dichloromethane, washed with 0.1N HCl, and brine. The solvent is evaporated, and the residue triturated with EtOAc, and the insoluble material filtered to give 207 mg of the product 189. 1H NMR (CDCl3) δ 8.56 (s, 1H), 7.50-7.20 (m, 5H), 5.15-4.95 (m, 2H), 4.35-4.05 (m, 2H), 2.85-2.55 (m, 1H), 2.25-2.05 (m, 1H), 1.90-1.05 (m, 15H); MS: m/z 330 (M++1).

Aufarbeitung

  1. custom(reaction block) overnight
  2. temperatureThe reaction mixture is cooled to RT
  3. washwashed with 0.1N HCl, and brine
  4. customThe solvent is evaporated
  5. customthe residue triturated with EtOAc
  6. filtrationthe insoluble material filtered

Quellen und Nachweise

ORD-Eintrag
ord-84efdb5d5dae460a81073ea222b46092
Quelldatensatz
uspto-grants-2008_02
Patentnummer
US07326792B2

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