Water → HCID 68308541, compound

HRID 2171651Notes

Reaction equation

HRID 2171651 reaction equation
[Si]([O:8][CH2:9][C:10]1[C:11]([F:22])=[C:12]([N:16]2[CH2:19][CH:18]([O:20][CH3:21])[CH2:17]2)[CH:13]=[CH:14][CH:15]=1)(C(C)(C)C)(C)C.C1COCC1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.O>CCOC(C)=O>[F:22][C:11]1[C:12]([N:16]2[CH2:17][CH:18]([O:20][CH3:21])[CH2:19]2)=[CH:13][CH:14]=[CH:15][C:10]=1[CH2:9][OH:8]

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 11078149TBAF tetrahydrofuranHCID 86686219HCID 86686219, compound

Product 1

HCID 68308541HCID 68308541, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-[3-({[tert-Butyl(dimethyl)silyl]oxy}methyl)-2-fluorophenyl]-3-methoxyazetidine (121 mg) was mixed with THF (4 ml), and a 1M TBAF/THF solution (0.8 ml) was added thereto, followed by stirring at room temperature for 1 hour. Water and EtOAc were added to the reaction mixture, and the organic layer was dried over Na2SO4 and concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography to obtain [2-fluoro-3-(3-methoxyazetidin-1-yl)phenyl]methanol (72 mg).

Workup

  1. dry with materialthe organic layer was dried over Na2SO4
  2. concentrationconcentrated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-862e3677e6c34788b02d698b124f595a
Source dataset
uspto-grants-2015_06
Patent number
US09051283B2

Reaction notes

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