Tetrabutylammonium Fluoride → (2S,5R)-tert-butyl 2-[(2-fluoro-6-nitrophenoxy)methyl]-5-(hydroxymethyl)morpholine-4-carboxylate
Reaction equation
[Si]([O:8][CH2:9][C@H:10]1[N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:14][C@@H:13]([CH2:23][O:24][C:25]2[C:30]([N+:31]([O-:33])=[O:32])=[CH:29][CH:28]=[CH:27][C:26]=2[F:34])[O:12][CH2:11]1)(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.CCOC(C)=O>[F:34][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]([N+:31]([O-:33])=[O:32])[C:25]=1[O:24][CH2:23][C@H:13]1[O:12][CH2:11][C@@H:10]([CH2:9][OH:8])[N:15]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:14]1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
To a solution of the product from step 2 (2.4 g, 4.8 mmol) in anhydrous THF (50 mL) under a nitrogen atmosphere was added a solution of tetra-n-butyl ammonium fluoride (1.0 M in THF, 9.6 mL) and the reaction mixture was stirred at ambient temperature for 2 h. The reaction mixture was diluted with EtOAc (200 mL) and washed with saturated solution of ammonium chloride (50 mL), brine (100 mL), dried (Na2SO4) and concentrated under reduced pressure. The residue was purified on a 40 g SiO2 column using a gradient elution of 20-50% EtOAc in hexanes. Fractions containing product were combined and the solvents were removed in vacuo to provide the product (1.6 g) as a yellow oil. LC MS: RT=3.66 min, M+H=387 (6 min gradient).
Workup
- washwashed with saturated solution of ammonium chloride (50 mL), brine (100 mL)
- dry with materialdried (Na2SO4)
- concentrationconcentrated under reduced pressure
- customThe residue was purified on a 40 g SiO2 column
- washa gradient elution of 20-50% EtOAc in hexanes
- additionFractions containing product
- customthe solvents were removed in vacuo
Sources & evidence
- ORD record
- ord-649daaf4e10d4e81843aace4f3514339
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09315475B2
Reaction notes
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