Iodobenzene diacetate → 4-Ethyl-4-methyltetrahydro-1,2,3-oxathiazine 2,2-dioxide
Reaction equation
[S:1](=[O:11])(=[O:10])([O:3][CH2:4][CH2:5][CH:6]([CH3:9])[CH2:7][CH3:8])[NH2:2].C(OI(C1C=CC=CC=1)OC(=O)C)(=O)C>ClCCl>[CH2:7]([C:6]1([CH3:9])[CH2:5][CH2:4][O:3][S:1](=[O:10])(=[O:11])[NH:2]1)[CH3:8]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
To a solution of 3-methylpentyl sulfamate from Step 1 (1.25 mmol) in 8 mL of dichloromethane was added sequentially MgO (116 mg, 30 mmol), PhI(OAc)2 (443 mg 1.4 mmol), and Rh2(oct)4 (20 mg, 0.025 mmol). The suspension was stirred vigorously and heated at 40° C. for 3 h. The reaction mixture was cooled to room temperature, diluted with 20 mL of dichloromethane, and filtered through a pad of Celite then concentrated. The crude product was purified by multiple flash chromatographies (5% ethyl acetate/dichloromethane) to give 4-ethyl-4-methyltetrahydro-1,2,3-oxathiazine 2,2-dioxide.
Workup
- temperatureThe reaction mixture was cooled to room temperature
- filtrationfiltered through a pad of Celite
- concentrationthen concentrated
- customThe crude product was purified by multiple flash chromatographies (5% ethyl acetate/dichloromethane)
Sources & evidence
- ORD record
- ord-9e7c6a85a7874d19b490444da2c40412
- Source dataset
- uspto-grants-2014_05
- Patent number
- US08722727B2
Reaction notes
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