Benzenesulfonyl chloride → 4-[2-(1-Benzenesulfonyl-piperidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 456463ノート

反応式

HRID 456463 の反応式
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH:21]2[CH2:26][CH2:25][CH2:24][N:23](C(OCC3C=CC=CC=3)=O)[CH2:22]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H][H].C(N(CC)CC)C.[C:46]1([S:52](Cl)(=[O:54])=[O:53])[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=1>CO.[Pd].C(OCC)(=O)C.C(Cl)Cl>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[O:20][CH:21]2[CH2:26][CH2:25][CH2:24][N:23]([S:52]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)(=[O:54])=[O:53])[CH2:22]2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

9

反応物 4

HCID 7369Benzenesulfonyl chlorideHCID 8471Triethylamine2 回HCID 694231604-[2-(1-Benzyloxycarbonyl-piperidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl esterHCID 178418361HCID 178418361、化合物

生成物 1

HCID 694221304-[2-(1-Benzenesulfonyl-piperidin-3-yloxy)-phenyl]-piperazine-1-carboxylic acid tert-butyl ester収率 82%

試薬・触媒・溶媒 4

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

The compound of Step 1 (2.5 g, 4.7 mmol) was dissolved in methanol (20 mL). Palladium on carbon (50% water, 2.1 g) was added. A hydrogen atmosphere was established using balloons, and the mixture was stirred at r.t. for about 4 hours. The catalyst was removed by filtration with ethyl acetate through a bed of celite. The compound was isolated by running scrub-plug with a gradient of 100% ethyl acetate (200 mL) to triethylamine in ethyl acetate (10%). The isolated product (0.36 g, 0.9 mmol) was dissolved in methylene chloride (10 mL) at 0° C., and triethylamine (0.38 mL, 2.7 mmol) was added. Benzenesulfonyl chloride (0.15 mL, 1.1 mmol) was added drop wise to the reaction mixture. The solution warmed to r.t., concentrated under reduced pressure and purified using silica gel chromatography (75% ethyl acetate in hexanes) to afford the final compound (0.400 g, 82%).

後処理

  1. customThe catalyst was removed by filtration with ethyl acetate through a bed of celite
  2. customThe compound was isolated
  3. temperatureThe solution warmed to r.t.
  4. concentrationconcentrated under reduced pressure
  5. custompurified

出典と根拠

ORDレコード
ord-c30e056c1f274e40a6386fd36084f046
出典データセット
uspto-grants-2007_03
特許番号
US07186715B2

反応ノート

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