Water → 1-Methyl-6-(4-methylbenzenesulfonyl)-6-azabicyclo[3.1.0]hexane

HRID 1750501

反応式

HRID 1750501 の反応式
[CH3:1][C:2]1[CH2:6][CH2:5][CH2:4][CH:3]=1.Cl[N-:8][S:9]([C:12]1[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10].[Na+].[Br-].[Br-].[Br-].C[N+](C)(C)C1C=CC=CC=1.C[N+](C1C=CC=CC=1)(C)C.C[N+](C1C=CC=CC=1)(C)C.O>C1COCC1>[CH3:1][C:2]12[N:8]([S:9]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][CH:13]=3)(=[O:10])=[O:11])[CH:6]1[CH2:5][CH2:4][CH2:3]2

参加物

6

反応物 4

HCID 962WaterHCID 127461-MethylcyclopenteneHCID 3641960Chloramine-THCID 17977687Phenyltrimethylammonium bromide dibromide

生成物 1

HCID 1180245801-Methyl-6-(4-methylbenzenesulfonyl)-6-azabicyclo[3.1.0]hexane

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
25 °C

実験手順

To a solution of 1-methylcyclopent-1-ene (CAS number 693-89-0; 50.0 g, 609.75 mmol) iii and sodium chloro(4-methylbenzenesulfonyl)azanide (CAS number 127-65-1; 192 g, 680.85 mmol) in THF (2500 ml) was added trimethylphenylammonium tribromide (13.3 g, 61.57 mmol). The reaction was stirred vigorously at 25° C. for 12 hours. The reaction mixture was poured into water (1500 ml) and the organics were extracted with ethyl acetate (3×1000 ml). The combined organics were washed with water (500 ml), brine (500 ml), dried over sodium sulfate and concentrated in vacuo. This was then purified by column chromatography (silica, 0-2.5% ethyl acetate/n-hexane) to afford the title compound.

後処理

  1. extractionthe organics were extracted with ethyl acetate (3×1000 ml)
  2. washThe combined organics were washed with water (500 ml), brine (500 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThis was then purified by column chromatography (silica, 0-2.5% ethyl acetate/n-hexane)

出典と根拠

ORDレコード
ord-3662870c197c4417a45b083481a04d69
出典データセット
uspto-grants-2015_10
特許番号
US09156829B2

関連ノート

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