Ammonium Chloride → 2-Cyclopropyl-7-(1-hydroxymethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile

HRID 17586노트

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HRID 17586 반응식
[C:1]([C:3]1[C:8]2[N:9]=[C:10]([CH:12]3[CH2:14][CH2:13]3)[O:11][C:7]=2[C:6]([CH:15]([CH2:20][CH:21]=[CH2:22])[C:16](OC)=[O:17])=[C:5]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:4]=1[CH3:29])#[N:2].[Li+].[B-](CC)(CC)CC.[Cl-].[NH4+]>O1CCCC1>[CH:12]1([C:10]2[O:11][C:7]3[C:8](=[C:3]([C:1]#[N:2])[C:4]([CH3:29])=[C:5]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:6]=3[CH:15]([CH2:16][OH:17])[CH2:20][CH:21]=[CH2:22])[N:9]=2)[CH2:13][CH2:14]1

참가 물질

5

반응물 3

HCID 25517Ammonium ChlorideHCID 23712863Lithium triethylborohydrideHCID 68584392Methyl 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)pent-4-enate

생성물 1

HCID 685849552-Cyclopropyl-7-(1-hydroxymethylbut-3-enyl)-5-methyl-6-phenyl-1,3-benzoxazole-4-carbonitrile수율 95%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

Methyl 2-(4-cyano-2-cyclopropyl-5-methyl-6-phenyl-1,3-benzoxazol-7-yl)pent-4-enate (I-296) (100 mg, 0.26 mmol) was dissolved in tetrahydrofuran (2 ml), then under nitrogen atmosphere at −78° C., Super Hydride (1.0 M tetrahydrofuran solution) (570 μl, 0.52 mmol) was dropwise added. After stirring at the same temperature for 2 hours, aqueous saturated ammonium chloride solution was added, followed by further stirring at room, temperature for 10 minutes. The solution was extracted three times with ethyl acetate. The organic layers were combined, washed with saturated brine, dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, the solvent was evaporated away, and the resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane:ethyl acetate=2:1, v/v) to obtain the entitled compound (88 mg, 95%) as a colorless gel.

후처리

  1. stirringby further stirring at room, temperature for 10 minutes
  2. extractionThe solution was extracted three times with ethyl acetate
  3. washwashed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe insoluble matter was separated by filtration
  6. customthe solvent was evaporated away
  7. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, n-hexane

출처 및 근거

ORD 기록
ord-36bf63e59d384b628941c7ed23c0d940
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737166B2

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