Sodium Sulfite → 2-Benzyl-3-iodo-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridine

HRID 2216342

반응식

HRID 2216342 반응식
[CH2:1]([C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][C@@H:17]([O:19][CH3:20])[C@H:16]([OH:21])[CH2:15]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I:22]N1C(=O)CCC1=O.S([O-])([O-])=O.[Na+].[Na+]>CN(C)C=O>[CH2:1]([C:8]1[C:13]([I:22])=[CH:12][CH:11]=[C:10]([N:14]2[CH2:18][C@@H:17]([O:19][CH3:20])[C@H:16]([OH:21])[CH2:15]2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

참가 물질

5

반응물 3

HCID 24437Sodium SulfiteHCID 120273N-IodosuccinimideHCID 111968722-Benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridine

생성물 1

HCID 113843072-Benzyl-3-iodo-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridine수율 93.4%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

To a mixture of 3.11 g of 2-benzyl-6-[(3R,4R)-3-hydroxy-4-methoxypyrrolidin-1-yl]pyridine and 10 ml of N,N-dimethylformamide, while stirring in an ice bath, was added dropwise 2.5 g of N-iodosuccinimide, and the resultant mixture was stirred overnight as it was. To this was added sodium sulfite and the reaction mixture was extracted with ethyl acetate-water, and the organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (30% ethyl acetate/hexane), to give 4.19 g of the title compound.

후처리

  1. extractionthe reaction mixture was extracted with ethyl acetate-water
  2. washthe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated
  5. customThe residue was purified by silica gel column chromatography (30% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-7f79858587ff48f09b85eedf4ca608c2
출처 데이터셋
uspto-grants-2006_09
특허 번호
US07112593B2

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