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1,2-Dimethoxyethane → (r/s)-3-(Tert-butoxycarbonylamino)-1-[4-phenyl-5-isoquinolinesulfonyl]pyrrolidine

HRID 1436030
ノート
印刷プレビュー

反応式

HRID 1436030 の反応式
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19](Br)=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:28]1(B(O)O)[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.COCCOC.C(=O)([O-])[O-].[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:13][CH2:12][N:11]([S:14]([C:17]2[C:18]3[C:19]([C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:20][N:21]=[CH:22][C:23]=3[CH:24]=[CH:25][CH:26]=2)(=[O:16])=[O:15])[CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 67242856(r/s)-3-(Tert-butoxycarbonylamino)-1-(4-bromo-5-isoquinolinesulfonyl)pyrrolidine

生成物 1

HCID 68587287(r/s)-3-(Tert-butoxycarbonylamino)-1-[4-phenyl-5-isoquinolinesulfonyl]pyrrolidine収率 69.7%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒
HCID 962Water溶媒

実験手順

Intermediate 1 (228 mg) obtained in Example 1, Step A is added with phenylboronic acid (122 mg, Aldrich), tetrakis(triphenylphosphine)palladium(0) (116 mg), 1,2-dimethoxyethane (5 ml) and 2 N aqueous sodium carbonate (2 ml), and the mixture is refluxed by heating for 5 hours under a nitrogen gas atmosphere. The reaction mixture is cooled to room temperature, then added with water (25 ml), and extracted 3 times with ethyl acetate (20 ml for each time), and the combined organic layer is washed with saturated brine (30 ml), and dried over anhydrous magnesium sulfate. The solvent is evaporated under reduced pressure, and the residue is purified by silica gel chromatography (n-hexane:ethyl acetate=2:1) to obtain the title compound (158 mg (predictive yield)).

後処理

  1. temperaturethe mixture is refluxed
  2. temperatureby heating for 5 hours under a nitrogen gas atmosphere
  3. extractionextracted 3 times with ethyl acetate (20 ml for each time), and the combined organic layer
  4. washis washed with saturated brine (30 ml)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent is evaporated under reduced pressure
  7. customthe residue is purified by silica gel chromatography (n-hexane:ethyl acetate=2:1)

出典と根拠

ORDレコード
ord-8500c50c94324066aebfccb1e913e58f
出典データセット
uspto-grants-2009_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07618984B2

反応ノート

読み込み中…

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