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

HRID 1667139Notes

Reaction equation

HRID 1667139 reaction equation
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]

Participants

5

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-17835fdea9d24958b018468383893b7f
Source dataset
uspto-grants-2011_10
Patent number
US08044069B2

Reaction notes

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