Water → 2-hydroxy-N-(5-methylpyridin-2-yl)hexanamide

HRID 1098074Notes

Reaction equation

HRID 1098074 reaction equation
CCCC[N+](CCCC)(CCCC)CCCC.O.O.O.[F-].[Si]([O:29][CH:30]([CH2:41][CH2:42][CH2:43][CH3:44])[C:31]([NH:33][C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][N:35]=1)=[O:32])(C(C)(C)C)(C)C.O.CCOC(C)=O>C1COCC1>[OH:29][CH:30]([CH2:41][CH2:42][CH2:43][CH3:44])[C:31]([NH:33][C:34]1[CH:39]=[CH:38][C:37]([CH3:40])=[CH:36][N:35]=1)=[O:32]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 575045712-{[tert-butyl(dimethyl)silyl]oxy}-N-(5-methylpyridin-2-yl)hexanamide

Product 1

HCID 574386192-hydroxy-N-(5-methylpyridin-2-yl)hexanamideYield 94.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tetrabutylammoniumfluoride trihydrate (302 mg, 0.96 mmol) was added to a stirred solution of 2-{[tert-butyl(dimethyl)silyl]oxy}-N-(5-methylpyridin-2-yl)hexanamide (Step 2) (215 mg, 0.64 mmol) in THF (5 mL). The reaction mixture was kept at ambient temperature for 1 h. Water and EtOAc were added and the two phases were separated. The organic phase was washed with water, dried over MgSO4 and concentrated in vacuo. The residue was purified with column chromatography (silica gel, eluting with DCM/EtOAc:2/1) to give the title compound as a colourless solid (135 mg), 1H NMR (300 MHz, CDCl3) δ 9.46 (br s, 1H), 8.20 (d, 1H), 8.04 (d, 1H), 7.55 (dd, 1H), 5.47 (br s, 1H), 4.29 (m, 1H), 2.31 (s, 3H), 1.98 (m, 1H), 1.76 (m, 1H), 1.52 (m, 2H), 1.38 (m, 2H), 0.92 (t, 3H).

Workup

  1. customthe two phases were separated
  2. washThe organic phase was washed with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified with column chromatography (silica gel, eluting with DCM/EtOAc:2/1)

Sources & evidence

ORD record
ord-d9897eabd5af47229fb31c830981a731
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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