Dichloromethane → HCID 178455586, compound

HRID 2278364Notes

Reaction equation

HRID 2278364 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].[CH2:19](Cl)Cl>S([O-])([O-])(=O)=O.[Cu+2]>[CH3:12][C:11]([CH3:14])([Si:8]([CH3:10])([CH3:9])[O:15][CH2:16][CH2:17]/[CH:19]=[N:7]/[S+:5]([O-:6])[C:2]([CH3:4])([CH3:3])[CH3:1])[CH3:13]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 11355477tert-Butylsulfinamide, (S)-(-)-

Product 1

HCID 178455586HCID 178455586, compound

Reagents, catalysts & solvents 1

HCID 24462Copper SulfateCatalyst

Procedure

A three necked round bottom flask fitted with a mechanical stirrer, nitrogen inlet and temperature probe was charged with (S)-(−)-2-methyl-2-propanesulfinamide (113 g, 0.929 mol) and DCM (2.0 L) at room temperature (endotherm to 9° C.). Copper(II) sulfate (309 g, 1.94 mol) was then added followed by (tert-butyldimethylsilyl-oxy)acetaldehyde (150 g, 0.774 mol). After 36 hours the reaction mixture was filtered through a plug of Celite, the plug rinsed with DCM (3×200 mL), and the filtrate concentrated to provide the title compound as a light yellow syrup. The crude product was carried forward into the next step without further purification. 1H NMR (CDCl3) δ 8.08 (1H, s), 4.56 (2H, s), 1.22 (9H, s), 0.95 (9H, s), 0.12 (6H, s).

Workup

  1. customA three necked round bottom flask fitted with a mechanical stirrer, nitrogen inlet
  2. filtrationAfter 36 hours the reaction mixture was filtered through a plug of Celite
  3. washthe plug rinsed with DCM (3×200 mL)
  4. concentrationthe filtrate concentrated

Sources & evidence

ORD record
ord-55ee6182529745c1be6414b6da09b902
Source dataset
uspto-grants-2015_09
Patent number
US09133157B2

Reaction notes

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