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Acrylonitrile → (+/-)-tert-butyl (1R,5S,65)-6-(2-cyanoethoxy)-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate

HRID 879205
ノート
印刷プレビュー

反応式

HRID 879205 の反応式
[OH:1][C@@H:2]1[C@H:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[C:5]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])[CH2:4][C@@H:3]1[CH3:25].[C:26](#[N:29])[CH:27]=[CH2:28].C(=O)([O-])[O-].[Cs+].[Cs+].C([O-])(O)=O.[Na+]>CC(O)(C)C.O>[C:26]([CH2:27][CH2:28][O:1][C@@H:2]1[C@H:7]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])[CH:6]=[C:5]([C:16]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[N+:22]([O-:24])=[O:23])[CH2:4][C@@H:3]1[CH3:25])#[N:29]
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

7

反応物 4

HCID 7855AcrylonitrileHCID 10796Cesium carbonateHCID 516892Sodium BicarbonateHCID 86705242(+/-)-Tert-butyl (1R,5S,6S)-6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate

生成物 1

HCID 86705253(+/-)-tert-butyl (1R,5S,65)-6-(2-cyanoethoxy)-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate収率 94%

試薬・触媒・溶媒

2
HCID 962Water溶媒HCID 6386tert-Butanol溶媒

反応条件

温度
35 °C

実験手順

A mixture of (+/−)-Tert-butyl (1R,5S,6S)-6-hydroxy-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate (1.0 equiv.), acrylonitrile (30.0 equiv.) and CESIUM CARBONATE (1.2 equiv.) in t-BuOH (0.57 M) was stirred at 35° C. for 3 hrs. The reaction was cooled to room temperature, followed by the addition of NaHCO3 (aq.) and water. The mixture was extracted with EtOAc and the combined organics were dried over MgSO4, filtered, and concentrated. The sample was purified by ISCO SiO2 chromatography to yield (+/−)-tert-butyl (1R,5S,6S)-6-(2-cyanoethoxy)-5-methyl-3-(3-nitropyridin-4-yl)cyclohex-2-enylcarbamate in 94% yield. LC/MS (m/z)=403.3 (MH+), Rt=0.92 min. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.13 (d, J=6.46 Hz, 3H), 1.46 (s, 9H), 1.99-2.18 (m, 2H), 2.20-2.36 (m, 1H), 2.65 (t, J=6.06 Hz, 2H), 3.68 (br. s., 1H), 3.88 (t, J=5.99 Hz, 2H), 4.51 (br. s., 1H), 4.99 (d, J=9.15 Hz, 1H), 5.39 (br. s., 1H), 7.25 (d, J=4.99 Hz, 1H), 8.73 (d, J=4.94 Hz, 1H), 9.10 (s, 1H).

後処理

  1. temperatureThe reaction was cooled to room temperature
  2. extractionThe mixture was extracted with EtOAc
  3. dry with materialthe combined organics were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe sample was purified by ISCO SiO2 chromatography

出典と根拠

ORDレコード
ord-f709f48f8c614ce4b59b34d8c2c1ba7a
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08987457B2

反応ノート

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