tert-Butanol → 1-Benzyl-3-(tritylamino)-2-azepanone

HRID 1269749

Reaction equation

HRID 1269749 reaction equation
[C:1]([NH:20][CH:21]1[CH2:27][CH2:26][CH2:25][CH2:24][NH:23][C:22]1=[O:28])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH2:31](Br)[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.C(O)(C)(C)C>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC.O>[CH2:31]([N:23]1[CH2:24][CH2:25][CH2:26][CH2:27][CH:21]([NH:20][C:1]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:22]1=[O:28])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Participants

8

Reactant 4

HCID 6386tert-ButanolHCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 147292183-(Tritylamino)-2-azepanone

Product 1

HCID 694310141-Benzyl-3-(tritylamino)-2-azepanoneYield 63%

Reagents, catalysts & solvents 3

HCID 67553Tetrabutylammonium IodideCatalystHCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 3-(tritylamino)-2-azepanone (2.85 g, 7.69 mmol) in tetrahydrofuran (30 ml) was added 60%-sodium hydride (462 mg, 11.6 mmol) at 0° C., and then stirred at room temperature for 30 minutes. Subsequently, a solution of benzyl bromide (1.0 ml, 8.41 mmol) in tetrahydrofuran (5 ml) was added dropwise thereto at room temperature over a period of 3 minutes, followed by adding thereto tetra-n-butylammonium iodide (57 mg, 0.15 mmol), and the resulting mixture was stirred at room temperature for 6 hours. The reaction mixture was cooled on an ice-water bath and t-butanol (0.7 ml) and water (1 ml) were added thereto at 0° C. The resulting mixture was poured into water and then extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: n-hexane/chloroform) to obtain 1-benzyl-3-(tritylamino)-2-azepanone (2.22 g, 63%).

Workup

  1. waitat room temperature over a period of 3 minutes
  2. additionby adding
  3. temperatureThe reaction mixture was cooled on an ice-water bath
  4. customat 0° C
  5. extractionextracted with ethyl acetate
  6. washThe organic layer was washed with a saturated aqueous sodium chloride solution
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe resulting residue was purified by a silica gel column chromatography (eluent: n-hexane/chloroform)

Sources & evidence

ORD record
ord-e20b0a807e764389869a1afb2e11ee16
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Linked notes

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