Tetrabutylammonium Fluoride → HCID 66852730, compound

HRID 2060791Notes

Reaction equation

HRID 2060791 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:16][CH:15]([O:17][Si](C(C)(C)C)(C)C)[CH2:14][CH:13]2[CH2:12][O:11][N:10]3[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=2[O:34][CH3:35])[CH:5]=[CH:6][C:7]=1[F:8].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1.ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([C:9]23[CH2:16][CH:15]([OH:17])[CH2:14][CH:13]2[CH2:12][O:11][N:10]3[CH2:25][C:26]2[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=2[O:34][CH3:35])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 57504919HCID 57504919, compound

Product 1

HCID 66852730HCID 66852730, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6a-(3-bromo-4-fluorophenyl)-5-(tert-butyldimethylsilyloxy)-1-(2,4-dimethoxybenzyl)hexahydro-1H-cyclopenta[c]isoxazole (3.00 g, 4.77 mmol) in THF (10 mL) is added 1 N tetrabutylammonium fluoride solution in THF (7.15 mL, 7.15 mmol). After stirring at room temperature for 2 hours, the reaction mixture is concentrated under reduced pressure to afford a residue that is diluted with dichloromethane and washed with water and brine. The organic layer is dried over sodium sulfate, filtered, and the filtrate is concentrated under reduced pressure to give a residue that is purified by silica gel chromatography eluting with a linear gradient of 0% to 10% methanol in dichloromethane over 20 minutes to give the title compound as a diastereomeric mixture (2.26 g, 100%). This mixture is purified again on silica gel chromatography to separate the diastereomers eluting with a linear gradient of 0% to 15% ethyl acetate in hexanes over 15 minutes to give the title compound as a racemic mixture (0.852 g, 37%). ES/MS m/e (79Br/81Br) 452, 454 (M+1).

Workup

  1. concentrationthe reaction mixture is concentrated under reduced pressure
  2. customto afford a residue that
  3. washwashed with water and brine
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customto give a residue that
  8. customis purified by silica gel chromatography
  9. washeluting with a linear gradient of 0% to 10% methanol in dichloromethane over 20 minutes

Sources & evidence

ORD record
ord-cde4c92a0d8a469db301d7e9c9ba1c01
Source dataset
uspto-grants-2012_10
Patent number
US08278441B2

Reaction notes

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