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

HRID 1029873ノート

反応式

HRID 1029873 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 of (3aR,7aR)-7,7-diphenyl-4-perhydroisoindolone hydrochloride (10 g) in dry dichloromethane (80 cc) cooled to +5° C. 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 a saturated aqueous solution (30 cc) of sodium bicarbonate; the organic phase is washed with distilled water (2 * 50 cc), dried over magnesium sulphate and filtered and the filtrate is concentrated to dryness under reduced pressure (2.7 kPa). The residue is crystallized from 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)-4-perhydroisoindolone (5.7 g) melting at 173° C. is obtained; [a]D20 =-282° (c=1, methanol).

後処理

  1. temperaturecooled to +5° C
  2. waitfor 20 hours at 20° C
  3. washthe organic phase is washed with distilled water (2 * 50 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 residue is crystallized from acetonitrile (15 cc)
  8. washwashed with acetonitrile (10 cc) and with isopropyl ether (10 cc)
  9. customdried

出典と根拠

ORDレコード
ord-5a04e955ef524053abcf1191b0d72169
出典データセット
uspto-grants-1992_04
特許番号
US05102667

反応ノート

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