Sodium triacetoxyborohydride → HCID 178452762, Verbindung

HRID 1852701Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1852701
[NH2:1][C:2]1[C:3]([Cl:17])=[N:4][C:5]([Cl:16])=[CH:6][C:7]=1[NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12].[CH3:18][C@H:19]1[CH2:24][CH2:23][C@H:22]([CH:25]=O)[CH2:21][CH2:20]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[Cl:17][C:3]1[C:2]([NH:1][CH2:18][C@H:19]2[CH2:24][CH2:23][C@H:22]([CH3:25])[CH2:21][CH2:20]2)=[C:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH:6]=[C:5]([Cl:16])[N:4]=1

Komponenten

6

Edukt 3

HCID 5049666Sodium triacetoxyborohydrideHCID 86724467Tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamateHCID 178461263HCID 178461263, Verbindung

Produkt 1

HCID 178452762HCID 178452762, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl (3-amino-2,6-dichloropyridin-4-yl)carbamate (353 g, 1.27 mol) and trans-4-methylcyclohexanecarbaldehyde (160 g, 1.27 mol) in DCM (8.0 L) and acetic acid (2 ml) was added sodium triacetoxyborohydride (807.7 g, 3.81 mol) at 0° C. The mixture was stirred for 15 min, and then warmed to room temperature. The mixture was stirred for 15 h at room temperature and then quenched with water (10 L). The mixture was filtered, the filtrate was separated, and the organic layer was concentrated under reduced pressure to give crude product. The crude product was purified over a silica gel column, eluting with EtOAc: petroleum ether (0-1:10), to give tert-butyl (2,6-dichloro-3-(((trans-4-methylcyclohexyl)methyl)amino)pyridin-4-yl)carbamate.

Aufarbeitung

  1. stirringThe mixture was stirred for 15 h at room temperature
  2. customquenched with water (10 L)
  3. filtrationThe mixture was filtered
  4. customthe filtrate was separated
  5. concentrationthe organic layer was concentrated under reduced pressure
  6. customto give crude product
  7. customThe crude product was purified over a silica gel column
  8. washeluting with EtOAc: petroleum ether (0-1:10)

Quellen und Nachweise

ORD-Eintrag
ord-197577fb1c9840ef8d9a77eebe3f4a91
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962611B2

Notizen zur Reaktion

Wird geladen…