1-Methyl-2-Oxy-5,5-Dimethyl Pyrrolidine → HCID 70925591, 화합물

HRID 1851654노트

반응식

HRID 1851654 반응식
F[C:2]1[CH:7]=[CH:6][C:5]([I:8])=[CH:4][N:3]=1.[CH3:9][N:10]1[C:14]([CH3:16])([CH3:15])[CH2:13][CH2:12][C:11]1=[O:17]>C1(C)C=CC=CC=1>[I:8][C:5]1[CH:6]=[CH:7][C:2]([CH:12]2[CH2:13][C:14]([CH3:16])([CH3:15])[N:10]([CH3:9])[C:11]2=[O:17])=[N:3][CH:4]=1

참가 물질

4

반응물 2

HCID 4445701-Methyl-2-Oxy-5,5-Dimethyl PyrrolidineHCID 27831792-Fluoro-5-iodopyridine

생성물 1

HCID 70925591HCID 70925591, 화합물수율 38%

시약·촉매·용매 1

HCID 1140Toluene용매2회

반응 조건

온도
-4 °C

실험 절차

A solution of 2-fluoro-5-iodopyridine (260 mg, 1.17 mmol) and 1,5,5-trimethyl-pyrrolidin-2-one (148 mg, 1.17 mmol) in 6 ml of dry toluene was purged with Argon and cooled to −4° C. A 1M solution of sodium hexamethyldisilylamide (NaHMDS) in toluene (2.33 ml, 2.33 mmol) was added dropwise maintaining the temperature below 0° C. The red solution was stirred for 2 h at 0° C., quenched by addition of 5 ml of saturated ammonium chloride solution. After extraction with ethyl acetate/water, drying over sodium sulfate and concentration; the residue (400 mg) was taken up in ethyl acetate, adsorbed onto 5 g of silicagel which was loaded onto a 20 g prepacked flash chromato-graphy column. After elution with a 0% to 75% ethyl acetate in heptane gradient, the fractions containing the desired product were collected to yield 145 mg (38%) of the title compound as a yellow viscous oil, MS: m/e=331.0 (M+H+).

후처리

  1. temperaturemaintaining the temperature below 0° C
  2. customquenched by addition of 5 ml of saturated ammonium chloride solution
  3. extractionAfter extraction with ethyl acetate/water
  4. dry with materialdrying over sodium sulfate and concentration
  5. washAfter elution with a 0% to 75% ethyl acetate in heptane gradient
  6. additionthe fractions containing the desired product
  7. customwere collected

출처 및 근거

ORD 기록
ord-cb26d2177d164cf6828dac2972911c36
출처 데이터셋
uspto-grants-2015_02
특허 번호
US08957213B2

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