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p-Toluenesulfonic acid → 4-(2-Methyl-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile

HRID 916348
ノート
印刷プレビュー

反応式

HRID 916348 の反応式
[CH3:1][CH:2]1[C:8](=O)[CH2:7][CH:6]2[N:10]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=3)[CH:3]1[CH2:4][CH2:5]2.C1(C)C=CC(S(NN)(=O)=O)=CC=1.C([BH3-])#N.[Na+].S1(CCCC1)(=O)=O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C(O)C.O.C1CCCCC1.CN(C)C=O>[CH3:1][CH:2]1[CH2:8][CH2:7][CH:6]2[N:10]([C:11]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14]([C:21]#[N:22])=[CH:13][CH:12]=3)[CH:3]1[CH2:4][CH2:5]2
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

10

反応物 5

HCID 6101p-Toluenesulfonic acidHCID 15303P-ToluenesulfonylhydrazideHCID 31347SulfolaneHCID 5003444Sodium cyanoborohydrideHCID 11644978HCID 11644978、化合物

生成物 1

HCID 117160474-(2-Methyl-8-azabicyclo[3.2.1]oct-8-yl)naphthalene-1-carbonitrile収率 22.9%

試薬・触媒・溶媒 4

HCID 702Ethanol溶媒HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8078Cyclohexane溶媒

反応条件

温度
110 °C

実験手順

159JP84 (115 mg, 0.40 mmol) and p-toluenesulfonhydrazide (90 mg, 0.48 mmol) in absolute ethanol (1.0 mL) were refluxed overnight and the resulting white precipitate was filtered off, dried in vacuo and added to a vial containing sodium cyanoborohydride (101 mg, 1.60 mmol), N,N-dimethylformamide (2.0 mL), sulfolane (2.0 mL), p-toluenesulfonic acid (25 mg) and cyclohexane (2.0 mL). The resulting solution was heated at 110° C. for 2 days, poured into water (200 mL), extracted with ethyl acetate (2×200 mL), dried over Na2SO4, filtered, concentrated in vacuo and purified by preparative TLC (ethyl acetate/n-heptane 1:5, 5× eluted) to afford the title compound (25.3 mg, 22%) as thick oil.

後処理

  1. filtrationthe resulting white precipitate was filtered off
  2. customdried in vacuo
  3. additionadded to
  4. extractionextracted with ethyl acetate (2×200 mL)
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by preparative TLC (ethyl acetate/n-heptane 1:5, 5× eluted)

出典と根拠

ORDレコード
ord-f54ceb6eab274363b2520803b0fb83a9
出典データセット
uspto-grants-2007_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07268232B2

反応ノート

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