Aniline → HCID 86649084、化合物

HRID 1099014ノート

反応式

HRID 1099014 の反応式
[C:1]1([CH:7]2[N:12]3[CH:8]2[CH:9](O)O[CH:11]3[CH:13]2[CH:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[NH:14]2)[CH:6]=[CH:5]C=CC=1.NC1C=CC=CC=1.[BH3-]C#N.[Na+].C([O-])(O)=O.[Na+]>CO.O.C(O)(=O)C>[C:7]1([NH:12][CH2:11][C@H:13]2[C@H:15]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[NH:14]2)[CH:1]=[CH:6][CH:5]=[CH:9][CH:8]=1

参加物

8

反応物 4

HCID 6115AnilineHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 250017156-Phenyl-2-(3-phenylaziridin-2-yl)-3-oxa-1-azabicyclo[3.1.0]hexan-4-ol

生成物 1

HCID 86649084HCID 86649084、化合物収率 99%

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

In a flamed-dried round bottom flask equipped with a rubber septum in order to maintain a nitrogen atmosphere was added 2a (58.8 mg, 0.2 mmol) and aniline (43.7 μl, 0.48 mmol) dissolved in 5 ml of anhydrous MeOH. The reaction was stirred for 10 minutes, then NaCNBH3 (40.2 mg, 0.64 mmol) was added. The reaction was allowed to stir for 5 hours while maintaining pH 7 through addition of acetic acid when required. NaHCO3 was then carefully added to the reaction mixture and stirred for 5 minutes. Water was added and the aqueous mixture was extracted 3 times with Et2O. The collected organic phases were washed with water, then brine, and dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified using flash column chromatography (silica gel; 5% MeOH in CH2Cl2) to afford the title compound as a white solid in 99% yield. Mp=96-97° C. 1H NMR (200 MHz. CDCl3) δ:7.40-7.10 (m, 7H), 6.78-6.62 (m, 3H), 3.51 (dd, J=13.6 Hz, 4.2 Hz, 1H), 3.4 (very bs, 2H), 3.28 (dd, J=13.6 Hz, 7.5 Hz, 1H), 2.86 (d, J=2.8 Hz, 1H), 2.50-2.35 (m, 1H) ppm. 13C NMR (50 MHz. CDCl3) δ: 148.3, 139.7, 129.5, 129.4, 128.8, 127.4, 125.8, 118.1, 115.3, 113.2, 46.4, 40.3, 38.0 ppm. Rf=0.14 (7:3 hexanes/EtOAc).

後処理

  1. customIn a flamed-dried round bottom flask equipped with a rubber septum in order
  2. temperatureto maintain a nitrogen atmosphere
  3. stirringto stir for 5 hours
  4. temperaturewhile maintaining pH 7
  5. stirringstirred for 5 minutes
  6. extractionthe aqueous mixture was extracted 3 times with Et2O
  7. washThe collected organic phases were washed with water
  8. dry with materialbrine, and dried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customThe crude product was purified

出典と根拠

ORDレコード
ord-1f22ec6e03f7438d8d2c7fffab164c41
出典データセット
uspto-grants-2012_03
特許番号
US08143375B2

反応ノート

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