Tetrahydrofuran → (S)-N-(4-(3,4-dichlorophenyl)butan-2-yl)-2-methylpropane-2-sulfinamide

HRID 1848383ノート

反応式

HRID 1848383 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10]/[CH:11]=[N:12]/[S@:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])[CH:5]=[CH:6][C:7]=1[Cl:8].[CH3:19][Mg]Br.C1COCC1>C(Cl)Cl.C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([CH2:9][CH2:10][CH:11]([NH:12][S@:13]([C:15]([CH3:18])([CH3:17])[CH3:16])=[O:14])[CH3:19])[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

6

反応物 3

HCID 8028TetrahydrofuranHCID 89477639(NE,S)-N-[3-(3,4-dichlorophenyl)propylidene]-2-methylpropane-2-sulfinamideHCID 178418573HCID 178418573、化合物

生成物 1

HCID 86728181(S)-N-(4-(3,4-dichlorophenyl)butan-2-yl)-2-methylpropane-2-sulfinamide収率 67%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

To a solution of Intermediate 16B (4.00 g, 13.1 mmol) in DCM (50 mL) was added slowly a solution of methylmagnesium bromide in toluene and THF (13.99 mL, 1.400 M, 19.59 mmol) and the reaction mixture was heated to reflux for 2.5 h. The reaction mixture was allowed to cool to rt and, diluted with DCM, washed with saturated NH4Cl, and the organic portion dried over MgSO4, filtered and concentrated. The residue was purified by ISCO chromatography (EtOAc/Hexanes 0-50% over 30 min, column 330 g, flow rate 100 mL/min) to give Intermediate 16C (2.80 g, 8.69 mmol, 67.0% yield) as a white solid. HPLC/MS (Method D) RT=1.12 min, [M+1]+ 322.1; Chiral HPLC (Method L) RT=4.55 min, PA=100%.

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2.5 h
  3. washwashed with saturated NH4Cl
  4. dry with materialthe organic portion dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by ISCO chromatography (EtOAc/Hexanes 0-50% over 30 min, column 330 g, flow rate 100 mL/min)

出典と根拠

ORDレコード
ord-24c493bb021d4840a648c3cdaade065f
出典データセット
uspto-grants-2015_02
特許番号
US08952180B2

反応ノート

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