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Triacetoxyperiodinane → 1-(3-Oxo-propyl)-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester

HRID 500962
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 500962
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][C:33]2[N:36]([CH2:49][CH2:50][CH2:51][OH:52])[N:37]=[C:38]([C:39]3[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:47])[F:46])=[CH:41][CH:40]=3)[C:32]=2[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl.CCOCC.C([O-])(O)=O.[Na+]>[C:23]([O:27][C:28]([N:30]1[CH2:35][CH2:34][C:33]2[N:36]([CH2:49][CH2:50][CH:51]=[O:52])[N:37]=[C:38]([C:39]3[CH:44]=[CH:43][C:42]([C:45]([F:48])([F:46])[F:47])=[CH:41][CH:40]=3)[C:32]=2[CH2:31]1)=[O:29])([CH3:26])([CH3:25])[CH3:24]
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Komponenten

6

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 684611921-(3-Hydroxy-propyl)-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester

Produkt 1

HCID 865848181-(3-Oxo-propyl)-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydro-pyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl esterAusbeute 79 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 3283
Diethyl Ether
Lösungsmittel
HCID 6344DichloromethaneLösungsmittel
HCID 516892Sodium BicarbonateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

Dess-Martin periodinane (1.43 g, 3.36 mmol) was added portion wise to a stirred solution of 1-(3-hydroxy-propyl)-3-(4-trifluoromethyl-phenyl)-1,4,6,7-tetrahydropyrazolo[4,3-c]pyridine-5-carboxylic acid tert-butyl ester (1.30 g, 3.05 mmol) in CH2Cl2 (15 mL) at 0° C. under N2. Then the reaction was stirred at 0° C. for 15 min and allowed to warm to room temperature. After stirring at room temperature for 1.5 h the reaction was diluted with Et2O (50 mL) and saturated NaHCO3 (15 mL) was added slowly (caution! gas evolution). Then Na2S2O3.5H2O (5.31 g, 21.4 mmol) was added and stirred for 30 min. The layers were separated and the aqueous layer was extracted with Et2O (2×30 mL). The combined extracts were washed with brine, dried (Na2SO4) and concentrated. MPLC (1-10% MeOH/CH2Cl2) afforded the aldehyde in 79% yield (1.02 g). TLC (silica, 10% MeOH/CH2Cl2): Rf=0.67. MS (electrospray) calculated for C21H24F3N3O3, 424.2 ([M+H]+), m/z found, 424.2. 1H NMR (400 MHz, CDCl3): 9.82 (s, 1H), 7.65 (br d, J=8.0 Hz, 2H), 7.54 (br s, 2H), 4.53 (s, 2H), 4.21 (t, J=6.2 Hz, 2H), 3.68 (br s, 2H), 3.04 (t, J=6.2 Hz, 2H), 2.70 (t, J=5.6 Hz, 2H), 1.39 (s, 9H).

Aufarbeitung

  1. temperatureto warm to room temperature
  2. stirringAfter stirring at room temperature for 1.5 h the reaction
  3. additionwas added slowly (caution! gas evolution)
  4. stirringstirred for 30 min
  5. customThe layers were separated
  6. extractionthe aqueous layer was extracted with Et2O (2×30 mL)
  7. washThe combined extracts were washed with brine
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-fcaa2d97d18d4995b33684fee60b4530
Quelldatensatz
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07772236B2

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