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

HRID 1426953Notes

Reaction equation

HRID 1426953 reaction equation
[CH3:1][C:2]([S@@:5]([NH2:7])=[O:6])([CH3:4])[CH3:3].[Si:8]([O:15][CH2:16][CH:17]=O)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]>C(Cl)Cl.S([O-])([O-])(=O)=O.[Cu+2]>[Si:8]([O:15][CH2:16]/[CH:17]=[N:7]/[S@:5]([C:2]([CH3:4])([CH3:3])[CH3:1])=[O:6])([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

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 73.4%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (S)-2-methylpropane-2-sulfinamide (3.3 g, 27.2 mmol) in DCM (50 mL) was added 2-(tert-butyldimethylsilyloxy)acetaldehyde (4.98 g, 28.6 mmol) followed by anhydrous copper sulfate (8.69 g, 54.5 mmol). The heterogeneous mixture was stirred at ambient temperature for 3 days and then filtered through Celite®. The filtrate concentrated and the residue was purified by flash column chromatography, eluting with 10% EtOAc/hexanes, to afford (S,E)-N-(2-(tert-butyldimethylsilyloxy)ethylidene)-2-methylpropane-2-sulfinamide (5.54 g, 73% yield) as a colorless oil. 1H NMR (CDCl3) δ 7.96 (m, 1H), 4.44 (d, 1H, J=2.7 Hz), 1.11 (s, 9H), 0.82 (s, 9H), 0.00 (s, 6H).

Workup

  1. filtrationfiltered through Celite®
  2. concentrationThe filtrate concentrated
  3. customthe residue was purified by flash column chromatography
  4. washeluting with 10% EtOAc/hexanes

Sources & evidence

ORD record
ord-d841638242524aa1b40c628b49bb4cc6
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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