Phenylacetyl chloride → (3aR,7aR)-7,7-Diphenyl-2-(phenylacetyl)perhydro-4-isoindolone

HRID 1196267ノート

反応式

HRID 1196267 の反応式
[C:1]1([CH2:7][C:8](Cl)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.Cl.[C:19]1([C:25]2([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C@H:33]3[C@H:29]([CH2:30][NH:31][CH2:32]3)[C:28](=[O:34])[CH2:27][CH2:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(=O)([O-])O.[Na+]>ClCCl>[C:35]1([C:25]2([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C@H:33]3[C@H:29]([CH2:30][N:31]([C:8](=[O:9])[CH2:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[CH2:32]3)[C:28](=[O:34])[CH2:27][CH2:26]2)[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

参加物

6

反応物 4

HCID 7679Phenylacetyl chlorideHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 22843247(3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride

生成物 1

HCID 22843240(3aR,7aR)-7,7-Diphenyl-2-(phenylacetyl)perhydro-4-isoindolone

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of phenylacetyl chloride (4 cc) and triethylamine (8.6 cc) in dichloromethane (10 cc) is added dropwise to a solution, cooled to +5° C., of (3aR,7aR)-7,7-diphenylperhydro-4-isoindolone hydrochloride (10 g) in dry dichloromethane (80 cc). The reaction mixture is stirred for 2 hours at +5° C. and then for 20 hours at 20° C. The reaction mixture is treated with saturated aqueous sodium hydrogen carbonate solution (30 cc); the organic phase is washed with distilled water (2×50 cc), dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized in acetonitrile (15 cc). The crystals are drained, washed with acetonitrile (10 cc) and with isopropyl ether (10 cc) and dried. (3aR,7aR)-7,7-Diphenyl-2-(phenylacetyl)perhydro-4-isoindolone (5.7 g), m.p. 173° C. is obtained; [α]D20 =-282° (c=1, methanol).

後処理

  1. waitfor 20 hours at 20° C
  2. washthe organic phase is washed with distilled water (2×50 cc)
  3. dry with materialdried over magnesium sulphate
  4. filtrationfiltered
  5. concentrationconcentrated to dryness under reduced pressure (2.7 kPa)
  6. customThe residue is crystallized in acetonitrile (15 cc)
  7. washwashed with acetonitrile (10 cc) and with isopropyl ether (10 cc)
  8. customdried

出典と根拠

ORDレコード
ord-8ebe565242554887a4be77d6e37a78d5
出典データセット
uspto-grants-1992_05
特許番号
US05112988

反応ノート

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