Ammonium Chloride → HCID 67714472、化合物

HRID 55411ノート

反応式

HRID 55411 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[Mg]Br.C([O:14][CH:15]1[CH2:23][C:22]([CH3:25])([CH3:24])[CH:21]2[CH:17]([CH2:18][N:19]([CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH2:20]2)[C:16]1=[O:33])(=O)C.[Cl-].[NH4+]>O1CCCC1.C(OCC)C>[CH2:26]([N:19]1[CH2:18][CH:17]2[CH:21]([C:22]([CH3:25])([CH3:24])[CH2:23][CH:15]([OH:14])[C:16]2([C:4]2[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=2[O:2][CH3:1])[OH:33])[CH2:20]1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

参加物

6

反応物 3

HCID 25517Ammonium ChlorideHCID 67714110(3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-dimethyl-4-perhydroisoindoloneHCID 178489560HCID 178489560、化合物

生成物 1

HCID 67714472HCID 67714472、化合物収率 35.1%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒HCID 8028Tetrahydrofuran溶媒2 回

実験手順

To a suspension of 33.8 g of 2-methoxyphenylmagnesium bromide in 75 cm3 of tetrahydrofuran is added dropwise, at room temperature and with stirring, a solution of 6.6 g of (3aRS,5RS,7aRS)-5-acetoxy-2-benzyl-7,7-dimethyl-4-perhydroisoindolone in 75 cm3 of tetrahydrofuran. The reaction mixture is stirred at room temperature for 15 hours, treated with 200 cm3 of saturated aqueous ammonium chloride solution and taken up in 200 cm3 of ethyl ether and 100 g of ice. The organic phase is extracted with 3 times 100 cm3 of ethyl ether, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in 500 cm3 of petroleum ether. 2.8 g of (3aRS,4RS,5RS,7aRS)-2-benzyl-7,7-dimethyl-4-(2-methoxyphenyl)-4,5-perhydroisoindolediol are obtained, melting at 190° C.

後処理

  1. additionis added dropwise, at room temperature
  2. stirringThe reaction mixture is stirred at room temperature for 15 hours
  3. extractionThe organic phase is extracted with 3 times 100 cm3 of ethyl ether
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe residue is crystallized in 500 cm3 of petroleum ether

出典と根拠

ORDレコード
ord-475038bb2b8a4fef9342ac505496ca28
出典データセット
uspto-grants-1997_04
特許番号
US05624950

反応ノート

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