Iodine → 3,4-dichloro-5-methyl-N-[(3S,4R)-3-(prop-2-en-1-yloxy)piperidin-4-yl]-1H-pyrrole-2-carboxamide

HRID 655757ノート

反応式

HRID 655757 の反応式
[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][N:15](C(OCC)=O)[CH2:14][C@@H:13]1[O:23][CH2:24][CH:25]=[CH2:26])=[O:10].II.C[Si](C)(C)[Si](C)(C)C.S([O-])([O-])(=O)=S.[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[C:6]([Cl:7])=[C:5]([CH3:8])[NH:4][C:3]=1[C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][NH:15][CH2:14][C@@H:13]1[O:23][CH2:24][CH:25]=[CH2:26])=[O:10]

参加物

6

反応物 4

HCID 807IodineHCID 24477Sodium ThiosulfateHCID 74057HexamethyldisilaneHCID 59402556Ethyl (3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidine-1-carboxylate2 回

生成物 1

HCID 594024493,4-dichloro-5-methyl-N-[(3S,4R)-3-(prop-2-en-1-yloxy)piperidin-4-yl]-1H-pyrrole-2-carboxamide収率 36.54%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

To as solution of Ethyl (3S,4R)-4-{[(3,4-dichloro-5-methyl-1H-pyrrol-2-yl)carbonyl]amino}-3-(prop-2-en-1-yloxy)piperidine-1-carboxylate (Intermediate 19, 2.5 g, 6.20 mmol) in toluene (450 mL) was added iodine (6.31 g, 24.8 mmol) followed by hexamethyldisilane (10.34 mL, 49.62 mmol and the reaction mixture was refluxed for 30 h. The reaction mixture was treated with 10% sodium thiosulphate (300 mL) and layers were separated. The aqueous layer was extracted with toluene and the organic layer was dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification by column chromatography (silica, 4% methanol in dichloromethane) afforded 750 mg (36.54%) of 3,4-dichloro-5-methyl-N-[(3S,4R)-3-(prop-2-en-1-yloxy)piperidin-4-yl]-1H-pyrrole-2-carboxamide.

後処理

  1. temperaturethe reaction mixture was refluxed for 30 h
  2. customwere separated
  3. extractionThe aqueous layer was extracted with toluene
  4. dry with materialthe organic layer was dried over anhydrous sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customPurification by column chromatography (silica, 4% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-b3875975125d4fbc88c8f958563a104d
出典データセット
uspto-grants-2011_12
特許番号
US08071605B2

反応ノート

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