N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamide → 2-Chloro-1-[3-(dimethylamino)phenyl]ethan-1-ol

HRID 2180327노트

반응식

HRID 2180327 반응식
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]([N:47]([CH3:49])[CH3:48])[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]([N:47]([CH3:49])[CH3:48])[CH:42]=1)[OH:40]

참가 물질

5

반응물 3

HCID 2734565N-((1R,2R)-2-Amino-1,2-diphenylethyl)-4-methylbenzene-1-sulfonamideHCID 224917802-Chloro-1-[3-(dimethylamino)phenyl]ethan-1-oneHCID 86592054potassium t-butoxide IPA

생성물 1

HCID 224917822-Chloro-1-[3-(dimethylamino)phenyl]ethan-1-ol수율 95.5%

시약·촉매·용매 1

HCID 3776Isopropanol용매

실험 절차

A solution of di-μ-chlorodichlorobis(pentamethylcyclopentadienyl)dirhodium (III) (1.5 mg, 0.0025 mmol) and (1R,2R)-N-(p-toluenesulfonyl)-1,2-diphenylethylenediamine (3.7 mg, 0.01 mmol) in isopropyl alcohol (4.75 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 (0.25 ml, 0.025 mmol) and 2-chloro-3′-(dimethylamino)acetophenone (98.8 mg, 0.5 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′-dimethylaminophenyl)ethanol (95.3 mg; yield: 95.3%; optical purity: 98.8% ee).

후처리

  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

출처 및 근거

ORD 기록
ord-908a04923063430dae1cd9244c0a371f
출처 데이터셋
uspto-grants-2005_05
특허 번호
US06888012B2

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