Tetrahydrofuran → HCID 178454066, 화합물

HRID 22942

반응식

HRID 22942 반응식
[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]

참가 물질

7

반응물 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 783082-Chloro-5-nitropyridineHCID 178418329HCID 178418329, 화합물

생성물 1

HCID 178454066HCID 178454066, 화합물수율 78%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-678dae14cca9433a8a259621d2e0eb49
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06849622B2

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