(-)-3-Hydroxytetrahydrofuran → 1-(2-((R)-tetrahydrofuran-3-yloxy)-5-nitrophenyl)-4-methyl-1H-tetrazol-5(4H)-one
Reaction equation
[OH:1][C@@H:2]1[CH2:6][CH2:5][O:4][CH2:3]1.CC(C)([O-])C.[K+].F[C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=1[N:23]1[C:27](=[O:28])[N:26]([CH3:29])[N:25]=[N:24]1>C1COCC1>[O:4]1[CH2:5][CH2:6][C@@H:2]([O:1][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][C:15]=2[N:23]2[C:27](=[O:28])[N:26]([CH3:29])[N:25]=[N:24]2)[CH2:3]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
(R)-(−)-3-Hydroxytetrahydrofuran (440 mg, 5 mmol, 2 equiv) in THF (15 ml) under argon gas, was cooled to 0° C. Potassium tert-butoxide (617 mg, 5.5 mmol, 2.2 equiv) was added in one portion, and the reaction mixture was stirred for 20 minutes at 0° C. Then 1-(2-fluoro-5-nitrophenyl)-4-methyl-1H-tetrazol-5(4H)-one (Described in: WO 2011/068898. 598 mg, 2.5 mmol, 1 equiv) was added in one portion, and the reaction mixture was stirred for 10 minutes at 0° C. and allowed to warm up to ambient temperature over 2 hours. The reaction mixture was concentrated, and the residue was taken in DCM and water. The layers were separated, and the organic layer was washed with water (×2), dried over Na2SO4, filtered, and concentrated to provide 1-(2-((R)-tetrahydrofuran-3-yloxy)-5-nitrophenyl)-4-methyl-1H-tetrazol-5(4H)-one (723 mg, 94%) as a yellow solid that was used without further purification.
Workup
- stirringthe reaction mixture was stirred for 10 minutes at 0° C.
- temperatureto warm up to ambient temperature over 2 hours
- concentrationThe reaction mixture was concentrated
- customThe layers were separated
- washthe organic layer was washed with water (×2)
- dry with materialdried over Na2SO4
- filtrationfiltered
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-1aed14eedfa74b04b9c685f96e9e960e
- Source dataset
- uspto-grants-2015_10
- Patent number
- US09169249B2
Reaction notes
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