2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → (NE,S)-N-[2-[tert-butyl(dimethyl)silyl]oxyethylidene]-2-methylpropane-2-sulfinamide

HRID 539069Notes

Reaction equation

HRID 539069 reaction equation
[Si:1]([O:8][CH2:9][CH:10]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH3:12][C:13]([S@@:16]([NH2:18])=[O:17])([CH3:15])[CH3:14]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[Si:1]([O:8][CH2:9]/[CH:10]=[N:18]/[S@:16]([C:13]([CH3:15])([CH3:14])[CH3:12])=[O:17])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 16007023(NE,S)-N-[2-[tert-butyl(dimethyl)silyl]oxyethylidene]-2-methylpropane-2-sulfinamideYield 94%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(tert-butyldimethylsilyloxy)acetaldehyde (54.64 mL, 258.2 mmol) in DCM (500 mL) was treated with (S)-2-methylpropane-2-sulfinamide (34.42 g, 284.0 mmol), followed by copper sulfate (103.0 g, 645.4 mmol) at ambient temperature. After stirring for 48 hours, the mixture was filtered through Celite and washed with DCM. The mixture was concentrated and purified on silica gel (10-30% EtOAc in hexane) to provide (S,E)-N-(2-(tert-butyldimethylsilyloxy)ethylidene)-2-methylpropane-2-sulfinamide (67.3 g, 94% yield).

Workup

  1. filtrationthe mixture was filtered through Celite
  2. washwashed with DCM
  3. concentrationThe mixture was concentrated
  4. custompurified on silica gel (10-30% EtOAc in hexane)

Sources & evidence

ORD record
ord-6037125acf1d47e19b299ee86ef3b61c
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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