2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → (R,E)-N-(2-((tert-butyldimethylsilyl)oxy)ethylidene)-2-methylpropane-2-sulfinamide

HRID 450370Notes

Reaction equation

HRID 450370 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.[O-]S([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 10964479tert-Butylsulfinamide, (R)-(+)-

Product 1

HCID 86644143(R,E)-N-(2-((tert-butyldimethylsilyl)oxy)ethylidene)-2-methylpropane-2-sulfinamide

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-2-methylpropane-2-sulfinamide (2.5 g, 20.6 mmol) and {[tert-butyl(dimethyl)silyl]oxy}acetaldehyde (4.32 ml, 22.7 mmol) in CH2Cl2 (30 ml) was added CuSO4 (7.23 g, 45.32 mmol). The reaction mixture was stirred at room temperature for 2 days. The mixture was filtered through Centel), washed with CH2Cl2 and concentrated in vacuo. Column chromatography (0-30% EtOAc in hexanes) gave the desired product (R)—N-(2-{[tert-butyl(dimethyl)silyl]oxy}ethylidene)-2-methylpropane-2-sulfinamide (Tetrahedron Lett. 2001, 42, 2051-54). 1H NMR (300 MHz, CDCl3) δ 7.86-8.24 (m, 1H) 4.53 (d, J=3.01 Hz, 2H) 1.15-1.23 (m, 9H) 0.90 (s, 9H) 0.08 (s, 6H).

Workup

  1. filtrationThe mixture was filtered through Centel),
  2. washwashed with CH2Cl2
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-281ffb10710046f1a09170c5e6613df6
Source dataset
uspto-grants-2013_07
Patent number
US08486966B2

Reaction notes

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