Sodium Bicarbonate → tert-Butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-1,4-diazepane-1-carboxylate

HRID 1807747Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1807747
[N:1]1([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Br[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([OH:32])([C:28]([F:31])([F:30])[F:29])[C:24]([F:27])([F:26])[F:25])=[CH:19][CH:18]=1.C(=O)([O-])O.[Na+]>C(#N)C>[F:25][C:24]([F:26])([F:27])[C:23]([C:20]1[CH:21]=[CH:22][C:17]([CH2:16][N:4]2[CH2:5][CH2:6][CH2:7][N:1]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:2][CH2:3]2)=[CH:18][CH:19]=1)([OH:32])[C:28]([F:29])([F:31])[F:30]

Komponenten

5

Edukt 3

HCID 516892Sodium BicarbonateHCID 2756058Tert-butyl 1,4-diazepane-1-carboxylateHCID 235273962-[4-(Bromomethyl)phenyl]-1,1,1,3,3,3-hexafluoropropan-2-ol

Produkt 1

HCID 86638560tert-Butyl 4-(4-(1,1,1,3,3,3-hexafluoro-2-hydroxypropan-2-yl)benzyl)-1,4-diazepane-1-carboxylateAusbeute 63,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

A mixture of tert-butyl 1,4-diazepane-1-carboxylate (24.52 mmol, 4.91 g), 2-(4-(bromomethyl)phenyl)-1,1,1,3,3,3-hexafluoropropan-2-ol (24.52 mmol, 8.26 g) and sodium hydrogencarbonate (36.8 mmol, 3.09 g) in acetonitrile (100 mL) was stirred for 24 hours then was concentrated under reduced pressure. Dichloromethane was added and the suspension was filtered. The filtrate was concentrated under reduced pressure. The residue was chromatographed on silica eluting with dichloromethane to dichloromethane/methanol (5%) to give the title compound (7.1 g). MS (ESI) m/z 457.2 [M+H]+

Aufarbeitung

  1. concentrationthen was concentrated under reduced pressure
  2. additionDichloromethane was added
  3. filtrationthe suspension was filtered
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customThe residue was chromatographed on silica eluting with dichloromethane to dichloromethane/methanol (5%)

Quellen und Nachweise

ORD-Eintrag
ord-3c9b728cc4a94539b578c54ab3790306
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08357679B2

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