Tetrabutylammonium Fluoride → HCID 24963684, compound

HRID 555382Notes

Reaction equation

HRID 555382 reaction equation
[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12](=[O:44])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]3[CH2:25][CH2:24][CH:23]([O:26][Si](C(C)(C)C)(C4C=CC=CC=4)C4C=CC=CC=4)[CH2:22][CH2:21]3)=[CH:15][CH:14]=1)[CH2:8]2.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[CH:1]12[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH:2]1[NH:11][C:12](=[O:44])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]3[CH2:21][CH2:22][CH:23]([OH:26])[CH2:24][CH2:25]3)=[CH:15][CH:14]=1)[CH2:8]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 66629630HCID 66629630, compound

Product 1

HCID 24963684HCID 24963684, compoundYield 27.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of N-adamantan-2-yl-4-[4-(t-butyl-diphenyl-silanyloxy)-cyclohexyloxy]-benzamide (4.73 g, 7.78 mmol) in dry THF (50 mL) was added a 1N TBAF solution in THF (31, 12 mL) and the mixture was stirred for 48 hrs. at room temperature. The volatiles were evaporated in vacuo and the residue redissolved in AcOEt (50 mL) and washed with 5% aqueous citric acid and vand. The organic phase was dried (MgSO4), filtered and the solvent evaporated in vacuo. The residue was purified using a Combi Flash Sq16× with a solvent gradient starting from AcOEt/heptan (20:80) to (85:15). Desired fractions were collected and the solvent evaporated in vacuo affording 780 mg (27%) of N-adamantan-2-yl-4-(4-hydroxy-cyclohexyloxy)-benzamide as a solid.

Workup

  1. customat room temperature
  2. customThe volatiles were evaporated in vacuo
  3. dissolutionthe residue redissolved in AcOEt (50 mL)
  4. washwashed with 5% aqueous citric acid and vand
  5. dry with materialThe organic phase was dried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent evaporated in vacuo
  8. customThe residue was purified
  9. customDesired fractions were collected
  10. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-61ff170f57f0440984daa9b23e90e61c
Source dataset
uspto-grants-2011_11
Patent number
US08053447B2

Reaction notes

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