Tetrabutylammonium Fluoride → 2-amino-5-(4-hydroxycyclohexyl)-N,N-dimethylbenzamide

HRID 511401Notes

Reaction equation

HRID 511401 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][CH:16]([O:19][Si](C(C)(C)C)(C)C)[CH2:15][CH2:14]2)=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[NH2:1][C:2]1[CH:12]=[CH:11][C:10]([CH:13]2[CH2:18][CH2:17][CH:16]([OH:19])[CH2:15][CH2:14]2)=[CH:9][C:3]=1[C:4]([N:6]([CH3:8])[CH3:7])=[O:5]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 672546822-amino-5-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-N,N-dimethylbenzamide2×

Product 1

HCID 672547852-amino-5-(4-hydroxycyclohexyl)-N,N-dimethylbenzamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 2-amino-5-(4-{[tert-butyl(dimethyl)silyl]oxy}cyclohexyl)-N,N-dimethylbenzamide (Compound 173B, 0.320 g, 0.850 mmol) in THF (2 mL) was charged with 1.0 M of tetra-n-butylammonium fluoride in THF (8.50 mL) and stirred at rt over night. The reaction mixture was partitioned between EtOAc and water and separated. The aqueous was extracted with EtOAc (3×) and the combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated. The compound was purified on an Isco Combiflash unit eluting with 75 to 100% EtOAc in heptane to afford the title compound. 1H NMR (400 MHz, DMSO-d6) δ 6.91-6.97 (m, 1H), 6.80-6.85 (m, 1H), 6.59-6.64 (m, 1H), 4.94 (s, 2H), 4.30 (d, J=3.79 Hz, 1H), 2.91 (s, 6H), 2.24-2.39 (m, 1H), 1.62-1.80 (m, 4H), 1.34-1.54 (m, 4H), 1.20-1.32 (m, 1H); MS (ES+): m/z: 263.15 [MH+]. HPLC: tR=2.84 min (Micromass ZQ3: polar—3 min).

Workup

  1. customThe reaction mixture was partitioned between EtOAc and water
  2. customseparated
  3. extractionThe aqueous was extracted with EtOAc (3×)
  4. washthe combined organic fractions were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe compound was purified on an Isco Combiflash unit
  9. washeluting with 75 to 100% EtOAc in heptane

Sources & evidence

ORD record
ord-2d5e5d48cc774fbfa315098a6c6b2d90
Source dataset
uspto-grants-2015_08
Patent number
US09096624B2

Reaction notes

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