Sodium borohydride → 4-[4-(3-Hydroxyisoindolin-1-on-2-yl)butylthio]pyridine

HRID 6155노트

반응식

HRID 6155 반응식
[C:1]1(=[O:22])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:4](=[O:17])[C:3]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:2]12.[BH4-].[Na+]>C(O)C>[OH:22][CH:1]1[C:2]2[C:3](=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:4](=[O:17])[N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1

참가 물질

4

반응물 2

HCID 4311764Sodium borohydrideHCID 14538888HCID 14538888, 화합물

생성물 1

HCID 190790764-[4-(3-Hydroxyisoindolin-1-on-2-yl)butylthio]pyridine수율 27.5%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 6.25 g (20.0 mol) of 4-(4-phthalimidobutylthio)pyridine in 300 ml of ethanol, 1.51 g (40 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 2.5 hours. The solvent was distilled off and saturated saline was added to the residue. The mixture was extracted with chloroform and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate) to give 1.73 g of the desired compound (27.5% yield, colorless crystals), mp. 144°-145° C.

후처리

  1. distillationThe solvent was distilled off
  2. additionsaturated saline was added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: ethyl acetate)

출처 및 근거

ORD 기록
ord-923c49f34b564c8dbe84a85dc91bb505
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246948

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