Sodium hydride → HCID 67378655、化合物

HRID 1182663ノート

反応式

HRID 1182663 の反応式
[H-].[Na+].[CH3:3][N:4]1[C:12](=[O:13])[CH:11]=[CH:10][N:9]2[C:5]1=[N:6][C@@H:7]1[CH2:16][CH2:15][CH2:14][C@@H:8]12.C1(C)C=CC(S([CH2:26][N+:27]#[C-:28])(=O)=O)=CC=1>C1COCC1>[CH3:3][N:4]1[C:12](=[O:13])[C:11]2=[CH:26][NH:27][CH:28]=[C:10]2[N:9]2[C@H:8]3[CH2:14][CH2:15][CH2:16][C@H:7]3[N:6]=[C:5]12

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 161915Tosylmethyl isocyanideHCID 67379018(3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-one

生成物 1

HCID 67378655HCID 67378655、化合物収率 94%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Sodium hydride (95%, 112 mg, 4.44 mmol) is suspended in 3 mL of anhydrous THF, and then a mixture of (3aS,8aR)-7-Methyl-1,2,3,3a,7,8a-hexahydro-3b,7,8-triaza-cyclopenta[a]inden-6-one (283 mg, 1.48 mmol) and p-toluenesulfonylmethyl isocyanide (97%, 347 mg, 1.77 mmol) in 5 mL of anhydrous THF is added dropwise. The mixture is stirred at room temperature for an hour, and then quenched with water. The mixture is extracted with CH2Cl2 (5×10 mL). The combined organic phase is washed with brine, and then dried with anhydrous Na2SO4. After filtration, the filtrate is evaporated to dryness under reduced pressure to give crude product (320 mg, yield 94%) as brown solids, which is used for the next reaction without further purification. MS (ESI) m/z 231.1 [M+H]+.

後処理

  1. additionis added dropwise
  2. customquenched with water
  3. extractionThe mixture is extracted with CH2Cl2 (5×10 mL)
  4. washThe combined organic phase is washed with brine
  5. dry with materialdried with anhydrous Na2SO4
  6. filtrationAfter filtration
  7. customthe filtrate is evaporated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-8b3379aba6824c2ba9d4af5816ce3efc
出典データセット
uspto-grants-2014_03
特許番号
US08664207B2

反応ノート

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