Triacetoxyperiodinane → 2-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetaldehyde

HRID 1667139

Reaktionsgleichung

Reaktionsgleichung von HRID 1667139
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][CH2:25][N:26]1[CH2:30][CH2:29][C:28]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:27]1=[O:43]>ClCCl.C(OCC)C>[O:43]=[C:27]1[C:28]([C:37]2[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=2)([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH2:29][CH2:30][N:26]1[CH2:25][CH:24]=[O:23]

Komponenten

5

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 673575371-(2-Hydroxyethyl)-3,3-diphenylpyrrolidin-2-one

Produkt 1

HCID 866408362-(2-Oxo-3,3-diphenylpyrrolidin-1-yl)acetaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of Dess-Martin periodinane (8.03 g, 18.92 mmol) in dichloromethane (100 mL) was added a solution of the product from Example 67A (4.84 g, 17.20 mmol) in dichloromethane (50 mL) at room temperature. After 30 minutes at room temperature, the reaction is diluted with diethyl ether, filtered and concentrated. Chromatography eluting with a gradient of 50% to 100% ethyl acetate/hexanes using a SF25-40 g (Analogix®, Burlington, Wis.) column gave the title compound. MS (DCI+) m/z 280.1 (M+H)+.

Aufarbeitung

  1. filtrationfiltered
  2. concentrationconcentrated
  3. washChromatography eluting with a gradient of 50% to 100% ethyl acetate/hexanes using a SF25-40 g (Analogix®, Burlington, Wis.) column

Quellen und Nachweise

ORD-Eintrag
ord-17835fdea9d24958b018468383893b7f
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08044069B2

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