Iodine → Hydroxy-di-thiophen-2-yl-acetic acid 1-methyl-piperidin-4-yl ester

HRID 551372노트

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HRID 551372 반응식
Br[C:2]1[S:3][CH:4]=[CH:5][CH:6]=1.[Mg].II.[CH3:10][N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18](=[O:26])[C:19](=[O:25])[C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[CH2:13][CH2:12]1.[Cl-].[NH4+]>C1COCC1>[CH3:10][N:11]1[CH2:16][CH2:15][CH:14]([O:17][C:18](=[O:26])[C:19]([OH:25])([C:20]2[S:21][CH:22]=[CH:23][CH:24]=2)[C:2]2[S:3][CH:4]=[CH:5][CH:6]=2)[CH2:13][CH2:12]1

참가 물질

7

반응물 5

HCID 807IodineHCID 138512-Bromothiophene2회HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 67196156Oxo-thiophen-2-yl-acetic acid 1-methyl-piperidin-4-yl ester

생성물 1

HCID 67195650Hydroxy-di-thiophen-2-yl-acetic acid 1-methyl-piperidin-4-yl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매3회

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온도
70 °C

실험 절차

A solution of 2-bromothiophene (3.2 ml, 33 mmol) in THF (30 ml) is added dropwise to a mixture of magnesium (0.8 g, 33 mmol) and a single crystal of iodine in THF (30 ml). After addition of just under one half of the 2-bromothiophene the addition is suspended until reaction has initiated (judged by an exotherm). The addition is then completed maintaining the reaction temperature to below 40° C. After the addition is completed the reaction mixture is heated to 70° C. for 1 hour. This mixture is then cooled and added to a solution of oxo-thiophen-2-yl-acetic acid 1-methyl-piperidin-4-yl ester (6.48 g, 25.6 mmol) in THF (80 ml). After the addition is completed the reaction mixture is stirred at room temperature for 1 hour and then heated to reflux for 2 hours. After cooling to room temperature saturated aqueous ammonium chloride solution (100 ml) is added. The solution is extracted with diethylether dried over magnesium sulphate, filtered and concentrated. Purification by flash silica column chromatography gives the title product.

후처리

  1. additionthe addition
  2. customis suspended until reaction
  3. additionThe addition
  4. temperatureis then completed maintaining the reaction temperature to below 40° C
  5. additionAfter the addition
  6. temperatureThis mixture is then cooled
  7. additionAfter the addition
  8. temperatureheated
  9. temperatureto reflux for 2 hours
  10. additionis added
  11. extractionThe solution is extracted with diethylether
  12. dry with materialdried over magnesium sulphate
  13. filtrationfiltered
  14. concentrationconcentrated
  15. customPurification by flash silica column chromatography

출처 및 근거

ORD 기록
ord-3cc90eddb9b74cdd94f445bae2c1c953
출처 데이터셋
uspto-grants-2011_05
특허 번호
US07947730B2

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