N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamide → 2-Chloro-1-(m-tolyl)ethanol

HRID 2180326ノート

反応式

HRID 2180326 の反応式
C1(C)C=CC(S(N[C@H](C2C=CC=CC=2)[C@@H](C2C=CC=CC=2)N)(=O)=O)=CC=1.C(O)(C)C.CC(C)([O-])C.[K+].[Cl:37][CH2:38][C:39]([C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([CH3:47])[CH:42]=1)=[O:40]>C(O)(C)C>[Cl:37][CH2:38][CH:39]([C:41]1[CH:46]=[CH:45][CH:44]=[C:43]([CH3:47])[CH:42]=1)[OH:40]

参加物

5

反応物 3

HCID 2734565N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamideHCID 222488212-Chloro-1-(3-methylphenyl)ethanoneHCID 86592054potassium t-butoxide IPA

生成物 1

HCID 137366742-Chloro-1-(m-tolyl)ethanol収率 93%

試薬・触媒・溶媒 1

HCID 3776Isopropanol溶媒2 回

実験手順

A solution of di-μ-chlorodichlorobis(pentamethylcyclopentadienyl)dirhodium (III) (3.1 mg, 0.005 mmol) and (1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (7.3 mg, 0.02 mmol) in isopropyl alcohol (5.0 ml) was heated at 80° C. for 20 minutes while stirring. After cooling the solution to room temperature, a 0.1 M potassium tert-butoxide isopropyl alcohol solution (0.5 ml, 0.05 mmol) and an isopropyl alcohol solution (4.5 ml) of 2-chloro-3′-methylacetophenone (168.6 mg, 1.0 mmol) as a reaction substrate were added thereto, followed by stirring at room temperature for 14 hours. After completion of the reaction, the solvent was removed by evaporation, and the residue was purified by silica gel column chromatography to give a desired compound, (+)-2-chloro-1-(3′-methylphenyl)ethanol (158.6 mg; yield: 93.0%; optical purity: 95.6% ee).

後処理

  1. additionsubstrate were added
  2. stirringby stirring at room temperature for 14 hours
  3. customAfter completion of the reaction
  4. customthe solvent was removed by evaporation
  5. customthe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-777a6211585b44e594935000f37cdc25
出典データセット
uspto-grants-2005_05
特許番号
US06888012B2

反応ノート

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