Methyl iodide → HCID 57868838, compound
Reaction equation
[CH:1]1([S:4]([N:7]2[CH2:10][CH:9]([O:11][Si:12]([CH2:17][CH3:18])([CH2:15][CH3:16])[CH2:13][CH3:14])[CH2:8]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1.[CH2:19]([Li])CCC.CCCCCC.CI>O1CCCC1>[CH3:19][C:1]1([S:4]([N:7]2[CH2:10][CH:9]([O:11][Si:12]([CH2:15][CH3:16])([CH2:17][CH3:18])[CH2:13][CH3:14])[CH2:8]2)(=[O:6])=[O:5])[CH2:3][CH2:2]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
To a solution of 1-(cyclopropylsulfonyl)-3-[(triethylsilyl)oxy]azetidine (1.0 g, 3.4 mmol) in tetrahydrofuran (20 mL) at −78° C. was added 2.50 M of n-butyllithium in hexane (1.37 mL, 3.43 mmol) dropwise. After stirring at this temperature for 1 hour, methyl iodide (0.224 mL, 3.60 mmol) was added. After 30 minutes, the reaction temperature was raised to 0° C. and stirred for 50 minutes. The reaction was quenched by the addition of saturated sodium bicarbonate, followed by brine and the product was extracted with ethyl acetate. The extracts were dried over sodium sulfate, decanted and concentrated. Flash column chromatography eluting with a gradient of 0-30% ethyl acetate in hexanes afforded product (890 mg, 85%).
Workup
- waitAfter 30 minutes
- stirringstirred for 50 minutes
- customThe reaction was quenched by the addition of saturated sodium bicarbonate
- extractionthe product was extracted with ethyl acetate
- dry with materialThe extracts were dried over sodium sulfate
- customdecanted
- concentrationconcentrated
- washFlash column chromatography eluting with a gradient of 0-30% ethyl acetate in hexanes afforded product (890 mg, 85%)
Sources & evidence
- ORD record
- ord-9845416ba1f94daf9e4af9903e466395
- Source dataset
- uspto-grants-2013_04
- Patent number
- US08420629B2
Reaction notes
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