Iodoethane → HCID 18539185, 화합물

HRID 412913노트

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HRID 412913 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH2:22](I)[CH3:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([S:14][C:15]2[CH:20]=[CH:19][C:18]([O:21][CH2:22][CH3:23])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

참가 물질

5

반응물 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 185387571-tert-Butoxycarbonyl-4-[(4-hydroxyphenyl)sulfanyl]piperidine

생성물 1

HCID 18539185HCID 18539185, 화합물수율 95.2%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
60 °C

실험 절차

A mixture of 1-tert-Butoxycarbonyl-4-[(4-hydroxyphenyl)sulfanyl]piperidine (3.09 g, 10.0 mmol), ethyl iodide (1.04 mL, 13.0 mmol), and potassium carbonate (1.80 g, 13.0 mmol) in DMF (15 mL) was stirred at 60° C. for 20 hours. The reaction mixture was evaporated under reduced pressure. The residue was diluted with ethyl acetate (40 mL), washed with water (10 mL), 0.5 N sodium hydroxide solution (10 mL×3), brine (10 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel, using ethyl acetate/hexane (1/19 to 1/9) as eluent to afford the title compound (3.21 g, 9.52 mmol, 95%) as a colorless oil.

후처리

  1. customThe reaction mixture was evaporated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate (40 mL)
  3. washwashed with water (10 mL), 0.5 N sodium hydroxide solution (10 mL×3), brine (10 mL)
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-9ae525ab10d842c0b02a0b8390a13d2c
출처 데이터셋
uspto-grants-2003_05
특허 번호
US06562978B1

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