Tributylstannane → 4-Benzoyloxy-1-methoxy-2,2,6,6-tetramethylpiperidine
Reaction equation
[CH2:1]([SnH](CCCC)CCCC)CCC.[C:14]([O:22][CH:23]1[CH2:28][C:27]([CH3:30])([CH3:29])[N:26]([OH:31])[C:25]([CH3:33])([CH3:32])[CH2:24]1)(=[O:21])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(I)I.ClC1C=CC=CC=1>C(OCC)(=O)C.CCCCCCC>[C:14]([O:22][CH:23]1[CH2:24][C:25]([CH3:33])([CH3:32])[N:26]([O:31][CH3:1])[C:27]([CH3:29])([CH3:30])[CH2:28]1)(=[O:21])[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Procedure
The reaction is carried out in a nitrogen atmosphere. Tributyltin hydride (20.0 grams, 68.7 mmol) is added dropwise over 2.75 hours to a solution, precooled to 10° C., of 40.0 grams (145 mmol) of 4-benzoyloxy-1-oxyl-2,2,6,6-tetramethylpiperidine, 9.0 grams (33.6 mmol) of methylene iodide (diiodomethane) and 75 ml of chlorobenzene. The reaction temperature reaches 27° C. during the addition. The red mixture is stirred at room temperature for 27 hours after the addition is complete. The reaction mixture is then passed through a column of silica gel (heptane, then 100:3 heptane:ethyl acetate). Fractions containing the desired product are concentrated to give a crude solid. Tributyltin iodide is removed by washing a solution of the crude solid with aqueous ammonia. Final purification by flash chromatography on silica gel (100:3 heptane:ethyl acetate) followed by recrystallization from heptane affords 4.8 grams of the title compound as a white solid melting at 126°-127° C.
Workup
- additionThe reaction temperature reaches 27° C. during the addition
- additionafter the addition
Sources & evidence
- ORD record
- ord-89f4e3447e92496383b4587eb15a2bfb
- Source dataset
- uspto-grants-1991_06
- Patent number
- US05021577
Reaction notes
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