Toluene → (2S,4R)-1-(3-pyridylmethyl)-2-formyl-4-(4-chlorophenylsulfonylamino)pyrrolidine

HRID 1077583ノート

反応式

HRID 1077583 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[CH2:12][C@H:11]([NH:13][S:14]([C:17]3[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=3)(=[O:16])=[O:15])[CH2:10][C@H:9]2[C:24](OC)=[O:25])[CH:2]=1.[H-].C([Al+]CC(C)C)C(C)C.C1(C)C=CC=CC=1.C(C(C(C([O-])=O)O)O)([O-])=O.[K+].[Na+]>C(Cl)Cl>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][N:8]2[CH2:12][C@H:11]([NH:13][S:14]([C:17]3[CH:18]=[CH:19][C:20]([Cl:23])=[CH:21][CH:22]=3)(=[O:15])=[O:16])[CH2:10][C@H:9]2[CH:24]=[O:25])[CH:2]=1

参加物

6

反応物 4

HCID 1140TolueneHCID 9855836Potassium sodium tartarateHCID 21225700DiisobutylaluminumhydrideHCID 57191432(2S,4R)-1-(3-pyridylmethyl)-2-methoxycarbonyl-4-(4-chlorophenyl-sulfonylamino)pyrrolidine

生成物 1

HCID 56987462(2S,4R)-1-(3-pyridylmethyl)-2-formyl-4-(4-chlorophenylsulfonylamino)pyrrolidine収率 112.2%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-50 °C

実験手順

In an atmosphere of nitrogen, (2S,4R)-1-(3-pyridylmethyl)-2-methoxycarbonyl-4-(4chlorophenylsulfonylamino)pyrrolidine (10 g, 0.0244 mol) was dissolved in methylene chloride (200 ml) and the solution was cooled to -50°~-55° C. Then, 1M diisobutylaluminum hydride in toluene (73.2 ml, 0.0732 mol) was added thereto dropwise at -50° C. and the mixture was stirred for 30 minutes. Then, 20% sodium potassium tartrate solution was added thereto at 25° C. for precipitation of insolubles. The insolubles were separated by filtration and washed with methylene chloride. The mother liquor and the washings were combined and, after phase separation, the methylene chloride layer was taken. The methylene chloride layer was concentrated to dryness to provide (2S,4R)-1-(3-pyridylmethyl)-2-formyl-4-(4-chlorophenylsulfonylamino)-pyrrolidine (10.4 g) as an oil.

後処理

  1. temperaturethe solution was cooled to -50°~-55° C
  2. customat 25° C. for precipitation of insolubles
  3. customThe insolubles were separated by filtration
  4. washwashed with methylene chloride
  5. customafter phase separation
  6. concentrationThe methylene chloride layer was concentrated to dryness

出典と根拠

ORDレコード
ord-a114289e3237442797c113e8718137a4
出典データセット
uspto-grants-1996_08
特許番号
US05543525

反応ノート

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