Triacetoxyperiodinane → [4-(Tert-butyldimethylsilanyloxy)-3-oxobutyl]carbamic acid tert-butyl ester

HRID 854702Notes

Reaction equation

HRID 854702 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[C:23]([O:27][C:28](=[O:43])[NH:29][CH2:30][CH2:31][CH:32]([OH:42])[CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36])([CH3:26])([CH3:25])[CH3:24]>ClCCl>[C:23]([O:27][C:28](=[O:43])[NH:29][CH2:30][CH2:31][C:32](=[O:42])[CH2:33][O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:36])[CH3:37])([CH3:26])([CH3:24])[CH3:25]

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 11508015[4-(Tert-butyldimethylsilanyloxy)-3-hydroxybutyl]carbamic acid tert-butyl ester

Product 1

HCID 11493428[4-(Tert-butyldimethylsilanyloxy)-3-oxobutyl]carbamic acid tert-butyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Dess-Martin periodinane (5.0 g, 11.8 mmol) in anhydrous dichloromethane (35 mL) at room temperature was added a solution of [4-(tert-butyldimethylsilanyloxy)-3-hydroxybutyl]carbamic acid tert-butyl ester (3.77 g, 11.8 mmol) in anhydrous dichloromethane. The resulting mixture was stirred at room temperature for one hour, evaporated in vacuo to one third of the initial volume and applied to a column packed with silica. Elution with ethyl acetate—petroleum ether solvent mixture afforded a colorless oil.

Workup

  1. customevaporated in vacuo to one third of the initial volume
  2. washElution with ethyl acetate—petroleum ether solvent mixture
  3. customafforded a colorless oil

Sources & evidence

ORD record
ord-c2623b95a37f45d6a851995d98abd758
Source dataset
uspto-grants-2007_08
Patent number
US07259271B2

Reaction notes

Loading…