Triethylamine → (3aRS,7aRS)-7,7-diphenyl-2-[(2,5-dimethoxyphenyl)acetyl]-4-perhydroisoindolone

HRID 1029894

反応式

HRID 1029894 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:4]=1[CH2:11][C:12]([OH:14])=O.Cl.[C:16]1([C:22]2([C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[CH:30]3[CH:26]([CH2:27][NH:28][CH2:29]3)[C:25](=[O:31])[CH2:24][CH2:23]2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.C(N(CC)CC)C>ClCCl>[C:32]1([C:22]2([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[CH:30]3[CH:26]([CH2:27][N:28]([C:12](=[O:14])[CH2:11][C:4]4[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:3]=4[O:2][CH3:1])[CH2:29]3)[C:25](=[O:31])[CH2:24][CH2:23]2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

参加物

5

反応物 3

HCID 8471TriethylamineHCID 744692,5-Dimethoxyphenylacetic acidHCID 212645437,7-Diphenylhexahydro-1H-isoindol-4(2H)-one hydrochloride

生成物 1

HCID 67915969(3aRS,7aRS)-7,7-diphenyl-2-[(2,5-dimethoxyphenyl)acetyl]-4-perhydroisoindolone収率 46.8%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

N,N'-Carbonyldiimidazole (1.14 g) is added to a solution of 2,5-dimethoxyphenylacetic acid (1.34 g) in dry dichloromethane (30 cc), cooled to +5° C. The mixture is stirred for 30 minutes at +5° C. and a solution of (3aRS,7aRS)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (2.28 g) and triethylamine (1.96 cc) in dichloromethane (20 cc) is then added. The reaction mixture is stirred at 20° C. for 16 hours, then washed with water (2×200 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The meringue obtained is crystallized from a mixture of acetonitrile (20 cc) and isopropyl ether (80 cc). The crystals are drained, washed with isopropyl ether (25 cc) and dried. (3aRS,7aRS)-7,7-diphenyl-2-[(2,5-dimethoxyphenyl)acetyl]-4-perhydroisoindolone (1.5 g) is obtained in the form of white crystals melting at 209° C.

後処理

  1. temperaturecooled to +5° C
  2. stirringThe reaction mixture is stirred at 20° C. for 16 hours
  3. washwashed with water (2×200 cc)
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure (2.7 kPa)
  7. customThe meringue obtained
  8. customis crystallized from a mixture of acetonitrile (20 cc) and isopropyl ether (80 cc)
  9. washwashed with isopropyl ether (25 cc)
  10. customdried

出典と根拠

ORDレコード
ord-039c8ca8f4f64ce991025dced8b95fb9
出典データセット
uspto-grants-1992_04
特許番号
US05102667

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