Tert-Butanesulfinamide → tert-Butyl 3-(((tert-butylsulfinyl)imino)methyl)azetidine-1-carboxylate

HRID 245979Notes

Reaction equation

HRID 245979 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH:12]=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:14][C:15]([S:18]([NH2:20])=[O:19])([CH3:17])[CH3:16]>C(Cl)Cl.[O-]S([O-])(=O)=O.[Cu+2]>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10](/[CH:12]=[N:20]/[S:18]([C:15]([CH3:17])([CH3:16])[CH3:14])=[O:19])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 3382465Tert-ButanesulfinamideHCID 10726182Tert-butyl 3-formylazetidine-1-carboxylate

Product 1

HCID 89421021tert-Butyl 3-(((tert-butylsulfinyl)imino)methyl)azetidine-1-carboxylateYield 81%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-formyl-azetidine-1-carboxylic acid tert-butyl ester (1.0 g, 5.4 mmol) and 2-methylpropane-2-sulfinamide (654 mg, 5.4 mmol) in dry CH2Cl2 (10 mL) was added anhydrous CuSO4 (1.9 g, 11.9 mmol). The heterogeneous reaction mixture was stirred at room temperature overnight then filtered over Celite, rinsing with CH2Cl2. The filtrate was concentrated and the resultant residue was absorbed onto SiO2 and purified by column chromatography with 20% to 40% EtOAc/hexanes to provide 1.26 g (81%) of 3-{[(E)-2-methyl-propane-2-sulfinylimino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester as a white solid.

Workup

  1. filtrationthen filtered over Celite
  2. washrinsing with CH2Cl2
  3. concentrationThe filtrate was concentrated
  4. customthe resultant residue was absorbed onto SiO2
  5. custompurified by column chromatography with 20% to 40% EtOAc/hexanes

Sources & evidence

ORD record
ord-3f2252c345b144bfb7daf8d3c3eb45b0
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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