Methylamine → HCID 69950662、化合物

HRID 428597ノート

反応式

HRID 428597 の反応式
[CH3:1][O:2][CH2:3][O:4][C@H:5]1[CH2:9][CH2:8][N:7]([CH2:10][C@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)O)[CH2:6]1.COCO[C@H]1CCN([C@H](C2C=CC=CC=2)CO)C1.CN.CS(Cl)(=O)=O.[H-].[Na+].[Cl:46][C:47]1[CH:48]=[C:49]([CH:52]=[CH:53][C:54]=1[NH:55][CH3:56])[C:50]#[N:51].[NH4+].[OH-]>C(Cl)Cl.CN(C)C=O.O>[Cl:46][C:47]1[CH:48]=[C:49]([CH:52]=[CH:53][C:54]=1[N:55]([C@@H:11]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:10][N:7]1[CH2:8][CH2:9][C@H:5]([O:4][CH2:3][O:2][CH3:1])[CH2:6]1)[CH3:56])[C:50]#[N:51]

参加物

11

反応物 7

HCID 6329MethylamineHCID 14923Ammonium HydroxideHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 15520998HCID 15520998、化合物HCID 15520999HCID 15520999、化合物HCID 159077543-Chloro-4-(methylamino)benzonitrile

生成物 1

HCID 69950662HCID 69950662、化合物収率 61%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

To a stirred solution of the mixture of 2-(3-(S)-methoxymethoxypyrrolidin-1-yl)-1-(S)-phenylethanol and 2-(3-(S)-methoxymethoxypyrrolidin-1-yl)-2-(R)-phenylethanol (251 mg, 1.00 mmol) and methylamine (0.167 ml, 1.20 mmol) in CH2Cl2 (4 ml) was added methanesulfonyl chloride (0.093 ml, 1.20 mmol) dropwise at 0° C. (ice bath). After 15.5 h stirring at room temperature, the reaction mixture was washed with saturated NaHCO3 aqueous solution, brine, dried (Na2SO4), and concentrated to give 238 mg of brown viscous oil-(i). To a suspension of NaH (48 mg, 1.20 mmol) in N,N-dimethylformamide (2 ml) was added a solution of 3-chloro-4-methylaminobenzonitrile (200 mg, 1.20 mmol) at room temperature. After stirring for 45 min, to this mixture was added a solution of the above brown viscous oil-(i) in N,N-dimethylformamide (2 ml) at room temperature and the mixture was stirred at room temperature for 4.5 h. H2O was added to this mixture, basified with 25%-NH4OH and extracted with CH2Cl2. The extract was washed with water, brine, dried (Na2SO4), and concentrated to give brown oil, which was purified by column chromatography (silica gel 20 g, CH2C2/MeOH 100/1-50/1) to afford 244 mg (61%) of brown oil.

後処理

  1. washthe reaction mixture was washed with saturated NaHCO3 aqueous solution, brine
  2. dry with materialdried (Na2SO4)
  3. concentrationconcentrated
  4. customto give 238 mg of brown viscous oil-(i)
  5. stirringAfter stirring for 45 min, to this mixture
  6. stirringthe mixture was stirred at room temperature for 4.5 h
  7. extractionextracted with CH2Cl2
  8. washThe extract was washed with water, brine
  9. dry with materialdried (Na2SO4)
  10. concentrationconcentrated
  11. customto give brown oil, which
  12. customwas purified by column chromatography (silica gel 20 g, CH2C2/MeOH 100/1-50/1)

出典と根拠

ORDレコード
ord-91bb1d04867b4f24833e10860a9329bb
出典データセット
uspto-grants-2001_11
特許番号
US06313302B2

反応ノート

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