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

HRID 1245772Notes

Reaction equation

HRID 1245772 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 colourless 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 colourless oil

Sources & evidence

ORD record
ord-66ec47c68fad44d89d1e2b575818f5d1
Source dataset
uspto-grants-2006_10
Patent number
US07125904B2

Reaction notes

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