Tetrahydrofuran → HCID 178454066、化合物

HRID 22942

反応式

HRID 22942 の反応式
[H-].[Na+].O1CCCC1.[C:8]([O:12][C:13]([NH:15][C@H:16]1[CH2:21][CH2:20][C@H:19]([OH:22])[CH2:18][CH2:17]1)=[O:14])([CH3:11])([CH3:10])[CH3:9].Cl[C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][N:25]=1>O.CS(C)=O>[C:8]([O:12][C:13]([NH:15][C@H:16]1[CH2:17][CH2:18][C@H:19]([O:22][C:24]2[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][N:25]=2)[CH2:20][CH2:21]1)=[O:14])([CH3:11])([CH3:9])[CH3:10]

参加物

7

反応物 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridineHCID 178418329HCID 178418329、化合物

生成物 1

HCID 178454066HCID 178454066、化合物収率 78%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

実験手順

2.04 g of 60% sodium hydride was gradually added to 150 ml of a tetrahydrofuran solution containing 10.0 g of trans-4-(tert-butoxycarbonylamino)cyclohexanol and 7.35 g of 2-chloro-5-nitropyridine, and 30 mL of dimethylsulfoxide was further added thereto, and then, the mixture was stirred at room temperature for 1 day. The reaction mixture was poured into water and extracted with chloroform. The extract was washed with water and brine, dried over anhydrous sodium sulfate, and then, the solvent was removed under reduced pressure. The residue was applied to silica gel column chromatography (solvent: chloroform alone to chloroform-ethyl acetate (20:1)). The obtained powder crystals were suspended in ethyl acetate-hexane mixed solution and collected by filtration to obtain 12.20 g of trans-1-tert-butoxycarbonylamino-4-(5-nitro-2-pyridyloxy)cyclohexane. To 10 ml of an ethanol suspension containing 800 mg of this compound was added 2 ml of 2N hydrochloric acid-dioxane solution, and the mixture was stirred at room temperature for 18 hours. The precipitates were collected by filtration to obtain 568 mg of trans-4-(5-nitro-2-pyridyloxy)cyclohexylamine.hydrochloride (Reference Example 9-1 in Table 6).

後処理

  1. additionwas further added
  2. extractionextracted with chloroform
  3. washThe extract was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. filtrationcollected by filtration

出典と根拠

ORDレコード
ord-678dae14cca9433a8a259621d2e0eb49
出典データセット
uspto-grants-2005_02
特許番号
US06849622B2

関連ノート

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