Tetrabutylammonium Fluoride → HCID 58291972, compound

HRID 1944726Notes

Reaction equation

HRID 1944726 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11]([C:13]2([OH:27])[CH2:18][CH2:17][CH:16]([O:19][Si](C(C)(C)C)(C)C)[CH2:15][CH2:14]2)=[O:12])[CH3:9])=[CH:4][CH:3]=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([NH:10][C:11]([C:13]2([OH:27])[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]2)=[O:12])[CH3:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 67224135HCID 67224135, compound2×

Product 1

HCID 58291972HCID 58291972, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-(tert-Butyl-dimethyl-silanyloxy)-1-hydroxy-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide (Intermediate 80, 700 mg) was treated with 1.0M TBAF in THF (3.0 ml) for 16 hours. The reaction was concentrated to reduce the volume of THF, then diluted with ethyl acetate. The organic layer was washed once with water followed by brine, then filtered and dried over sodium sulfate. The resulting residue was suspended in a minimum of dichloromethane and the resulting precipitate was isolated by filtration to yield a single diastereomer of 1,4-dihydroxy-cyclohexanecarboxylic acid [(R)-1-(4-fluoro-phenyl)-ethyl]-amide (132 mg). MS MH+ 282.4

Workup

  1. concentrationThe reaction was concentrated
  2. additiondiluted with ethyl acetate
  3. washThe organic layer was washed once with water
  4. filtrationfiltered
  5. dry with materialdried over sodium sulfate
  6. customthe resulting precipitate was isolated by filtration

Sources & evidence

ORD record
ord-f188a9e68e0e4c6ab60ad5e13c2469c9
Source dataset
uspto-grants-2013_03
Patent number
US08394858B2

Reaction notes

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