tert-Butyl 3-(((tert-butylsulfinyl)imino)methyl)azetidine-1-carboxylate → 3-[1-(2-Methyl-propane-2-sulfinylamino)-ethyl]-azetidine-1-carboxylic acid tert-butyl ester
Reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10](/[CH:12]=[N:13]/[S:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:20][Mg]Br>C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([CH:12]([NH:13][S:14]([C:16]([CH3:19])([CH3:18])[CH3:17])=[O:15])[CH3:20])[CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 3-{[(E)-2-methyl-propane-2-sulfinylimino]-methyl}-azetidine-1-carboxylic acid tert-butyl ester (0.25 g, 0.87 mmol) in CH2Cl2 (4 mL) at 0° C. was added dropwise methylmagnesium bromide (3.0 M in Et2O, 0.35 mL, 1.04 mmol). The reaction mixture was stirred at 0° C. for 1 h then quenched with saturated aqueous NH4Cl, diluted with water and extracted with EtOAc (2×). The combined organics were dried over MgSO4 and concentrated to afford 273 mg of 3-[1-(2-methyl-propane-2-sulfinylamino)-ethyl]-azetidine-1-carboxylic acid tert-butyl ester as an off-white foamy solid which was used without further purification.
Workup
- customthen quenched with saturated aqueous NH4Cl
- additiondiluted with water
- extractionextracted with EtOAc (2×)
- dry with materialThe combined organics were dried over MgSO4
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-6e412754ac0e44858eb7cad5fda4d52b
- Source dataset
- uspto-grants-2014_02
- Patent number
- US08658646B2
Reaction notes
Loading…