Triacetoxyperiodinane → [2-(2-Oxopiperidin-1-yl)phenyl]acetaldehyde

HRID 2178520Notes

Reaction equation

HRID 2178520 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N:32]1[CH2:37][CH2:36][CH2:35][CH2:34][C:33]1=[O:38]>ClCCl>[O:38]=[C:33]1[CH2:34][CH2:35][CH2:36][CH2:37][N:32]1[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][C:26]=1[CH2:25][CH:24]=[O:23]

Participants

4

Reactant 2

HCID 159087Triacetoxyperiodinane2×HCID 895002661-[2-(2-Hydroxyethyl)phenyl]piperidin-2-one

Product 1

HCID 89500863[2-(2-Oxopiperidin-1-yl)phenyl]acetaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess Martin periodinane (3.36 g, 7.91 mmol, 1.3 eq) is added portionwise under stirring to 1-[2-(2-hydroxyethyl)phenyl]piperidin-2-one a2-2 (1.33 g, 6.09 mmol, 1 eq) in dichloromethane (40 ml). After a few hours additional Dess Martin periodinane (1.29 g, 3.04 mmol, 0.5 eq) is added and the reaction mixture is stirred overnight at room temperature, then filtrated and evaporated to dryness to afford crude [2-(2-oxopiperidin-1-yl)phenyl]acetaldehyde a3-1, which is used in the next step without any further purification.

Workup

  1. filtrationfiltrated
  2. customevaporated to dryness

Sources & evidence

ORD record
ord-e97072b01d35494bae97fdf028580856
Source dataset
uspto-grants-2015_06
Patent number
US09067930B2

Reaction notes

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