Potassium Carbonate → (1R,2S)-[2-({[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-methyl)-cyclohexyl]-carbamic Acid Benzyl Ester

HRID 1592326ノート

反応式

HRID 1592326 の反応式
[CH2:1]([O:8][C:9]([NH:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]1[CH2:18]OS(C1C=CC(C)=CC=1)(=O)=O)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:30][C:31]1[CH:36]=[CH:35][C:34]([CH2:37][CH2:38][CH2:39][NH:40][CH3:41])=[CH:33][CH:32]=1.C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:8][C:9](=[O:10])[NH:11][C@@H:12]1[CH2:17][CH2:16][CH2:15][CH2:14][C@H:13]1[CH2:18][N:40]([CH2:39][CH2:38][CH2:37][C:34]1[CH:33]=[CH:32][C:31]([F:30])=[CH:36][CH:35]=1)[CH3:41])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 110842664-Fluoro-N-methyl-benzenepropanamineHCID 86599633toluene-4-sulfonic acid (1R,2R)-2-benzyloxycarbonylamino-cyclohexylmethyl Ester

生成物 1

HCID 69424744(1R,2S)-[2-({[3-(4-fluoro-phenyl)-propyl]-methyl-amino}-methyl)-cyclohexyl]-carbamic Acid Benzyl Ester収率 64.2%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

A solution of toluene-4-sulfonic acid (1R,2R)-2-benzyloxycarbonylamino-cyclohexylmethyl ester (632 mg, 1.51 mmol) in acetone (8 mL) was treated with N-[3-(4-fluorophenyl)-propyl]-methylamine (253 mg, 1.51 mmol) and potassium carbonate (209 mg, 1.51 mmol) and heated at reflux for 23.5 hours. The mixture was cooled and filtered, the solid was rinsed with acetone, and the filtrate was concentrated to provide a yellow-orange oil. Flash chromatography on silica gel, eluting with 50% ethyl acetate in hexane, followed by 50% ethyl acetate in hexane containing 5% ethanol, provided a light yellow viscous oil (400 mg, 64%).

後処理

  1. temperatureheated
  2. temperatureat reflux for 23.5 hours
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. washthe solid was rinsed with acetone
  6. concentrationthe filtrate was concentrated
  7. customto provide a yellow-orange oil
  8. washFlash chromatography on silica gel, eluting with 50% ethyl acetate in hexane

出典と根拠

ORDレコード
ord-779c18c5f592407a92d88f979c604e3e
出典データセット
uspto-grants-2007_11
特許番号
US07291744B2

反応ノート

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