Water → tert-butyl methyl(2-(methyl((3-(4-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)carbamate

HRID 570780Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 570780
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:14](C=O)=[CH:13][N:12]([CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)[N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH3:23][N:24]([CH2:32][CH2:33][NH:34][CH3:35])[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28].[BH3-][C:37]#N.[Na+].O>CO.[Cl-].[Cl-].[Zn+2]>[CH3:23][N:24]([CH2:32][CH2:33][N:34]([CH3:37])[CH2:35][C:14]1[C:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)=[N:11][N:12]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[CH:13]=1)[C:25](=[O:31])[O:26][C:27]([CH3:30])([CH3:29])[CH3:28]

Komponenten

7

Edukt 4

HCID 962WaterHCID 5003444Sodium cyanoborohydrideHCID 14403871tert-Butyl methyl(2-(methylamino)ethyl)carbamateHCID 904258773-(4-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehyde

Produkt 1

HCID 90425474tert-butyl methyl(2-(methyl((3-(4-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)carbamateAusbeute 89,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3007855ZincchlorideKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

To a solution of 3-(4-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-4-carbaldehyde (0.550 g, 0.00182 mol) in methanol (10 mL) at room temperature were added TEA (221 mg, 0.00913 mol), ZnCl2 (0.025 g, 0.000182 mol) and tert-butyl methyl(2-(methylamino)ethyl)carbamate (0.410 g, 0.00219 mol) and stirred for 45 min. NaCNBH3 (0.580 g, 0.00913 mol) was added and the reaction mixture was stirred for 2 h at room temperature. The reaction was poured into water (70 mL) and extracted with EtOAc (70 mL×2). The combined extracts were washed with brine (100 mL), dried over sodium sulphate and concentrated under vacuum. The residue was purified by SGC using DCM:MeOH (0%-4%) as eluent to obtain tert-butyl methyl(2-(methyl((3-(4-nitrophenyl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)methyl)amino)ethyl)carbamate (0.770 g, Yield: 86.71%). LCMS (ESI): RT=2.00 min, m/z=474.8 [M+F1]+.

Aufarbeitung

  1. stirringthe reaction mixture was stirred for 2 h at room temperature
  2. extractionextracted with EtOAc (70 mL×2)
  3. washThe combined extracts were washed with brine (100 mL)
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated under vacuum
  6. customThe residue was purified by SGC

Quellen und Nachweise

ORD-Eintrag
ord-d927fbb8382b456ca85eae39ca869764
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09023883B2

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