Tetrahydrofuran → 1-(Diphenylmethyl)azetidin-3-ol
Reaction equation
[C:1]1([CH:7]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:8]2[CH2:11][CH:10]([O:12]S(C)(=O)=O)[CH2:9]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1COCC1.C[Mg]Br>C(OCC)C>[CH:7]([N:8]1[CH2:11][CH:10]([OH:12])[CH2:9]1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
A solution of 1-(diphenylmethyl)-3-(methanesulphonyloxy) azetidine (1.0 g) in. THF (17 mL) was treated with 3.0 M methylmagnesium bromide (1.2 mL) in diethyl ether at 0° C. The reaction was stirred for 1.5 hours at 0° C. and then quenched with saturated aqueous sodium bicarbonate, filtered through Celite, and concentrated. The residue was then take up in methylene chloride and washed with saturated aqueous sodium bicarbonate, followed by brine. The organic layer was dried over magnesium sulfate, filtered, concentrated and purified by column chromatography (0 to 60% EtOAc/hexanes) to provide 640 mg of the title compounds as a clear, yellow oil. ESMS: 240.19 (M+1), 1.22 minutes, Method D.
Workup
- customquenched with saturated aqueous sodium bicarbonate
- filtrationfiltered through Celite
- concentrationconcentrated
- washwashed with saturated aqueous sodium bicarbonate
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated
- custompurified by column chromatography (0 to 60% EtOAc/hexanes)
Sources & evidence
- ORD record
- ord-e556365e962140cab8653ad10489b03c
- Source dataset
- uspto-grants-2009_12
- Patent number
- US07625909B2
Reaction notes
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