Potassium Carbonate → 1-Boc-4-(3-nitro-6-pentafluoroethyl-phenoxymethyl)-piperidine

HRID 238443노트

반응식

HRID 238443 반응식
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[CH:8][C:9]([C:13]([F:19])([F:18])[C:14]([F:17])([F:16])[F:15])=[C:10]([OH:12])[CH:11]=1)([O-:5])=[O:4].[C:20]([N:27]1[CH2:32][CH2:31][CH:30]([CH2:33]OS(C)(=O)=O)[CH2:29][CH2:28]1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.[OH-].[Na+]>[C:20]([N:27]1[CH2:28][CH2:29][CH:30]([CH2:33][O:12][C:10]2[C:9]([C:13]([F:18])([F:19])[C:14]([F:15])([F:16])[F:17])=[CH:8][CH:7]=[C:6]([N+:3]([O-:5])=[O:4])[CH:11]=2)[CH2:31][CH2:32]1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21]

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 2765838Tert-butyl 4-(methylsulfonyloxymethyl)piperidine-1-carboxylateHCID 17756181Phenol, 5-nitro-2-(1,1,2,2,2-pentafluoroethyl)-

생성물 1

HCID 219594131-Boc-4-(3-nitro-6-pentafluoroethyl-phenoxymethyl)-piperidine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매3회HCID 14798Sodium Hydroxide용매

실험 절차

To a slurry of 60% NaH suspension in DMF (30 mL) at RT added a solution of 5-nitro-2-pentafluoroethyl-phenol (3.6 g) in 5 mL DMF. The dark red mixture was stirred at RT for 10 min then added a solution of 1-Boc-4-methylsulfonyloxymethyl-piperidine (3.1 g) in 5 mL DMF. The reaction was stirred at 60° C. and 95° C. After 1 h, added 2.94 g K2CO3 and stirred overnight at 105° C. After cooling to RT, the reaction was diluted with hexanes and 1N NaOH. Separated layers, and washed organic layer with 1N NaOH and with brine, dried over Na2SO4, filtered and concentrated in vacuo. Purification with silica gel column chromatography with 8% EtOAc/Hexanes yielded 1-Boc-4-(3-nitro-6-pentafluoroethyl-phenoxymethyl)-piperidine as a light yellow thick oil.

후처리

  1. stirringThe reaction was stirred at 60° C. and 95° C
  2. waitAfter 1 h
  3. stirringstirred overnight at 105° C
  4. temperatureAfter cooling to RT
  5. washSeparated layers, and washed organic layer with 1N NaOH
  6. dry with materialwith brine, dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification with silica gel column chromatography with 8% EtOAc/Hexanes

출처 및 근거

ORD 기록
ord-7a46f3e07de449ada5eabbfbdfc662ea
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642624B2

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