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llms.txt · MCP 가이드개인정보처리방침 · 이용약관 · 지원v1.8.0
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Methyl iodide → methyl 3-{2-[(1R)-1-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]propyl}oxy)ethyl]phenyl}-2-methylpropanoate

HRID 1920793
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HRID 1920793 반응식
[CH:1](NC(C)C)(C)C.C([Li])CCC.CCCCCC.[Si:19]([O:26][C@H:27]([CH2:44][N:45]1[CH2:49][CH2:48][CH2:47][C@H:46]1[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([CH3:57])=[C:53]([F:58])[CH:52]=1)[CH2:28][O:29][C@@H:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38][CH2:39][C:40]([O:42][CH3:43])=[O:41])[CH3:31])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].CI>O1CCCC1.O>[Si:19]([O:26][C@H:27]([CH2:44][N:45]1[CH2:49][CH2:48][CH2:47][C@H:46]1[CH2:50][C:51]1[CH:56]=[CH:55][C:54]([CH3:57])=[C:53]([F:58])[CH:52]=1)[CH2:28][O:29][C@@H:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][C:33]=1[CH2:38][CH:39]([CH3:1])[C:40]([O:42][CH3:43])=[O:41])[CH3:31])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]
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참가 물질

8

반응물 5

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 8058HexaneHCID 58581161Methyl 3-{2-[(1R)-1-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]propyl}oxy)ethyl]phenyl}propanoateHCID 178418339Butyllithium

생성물 1

HCID 58580868
methyl 3-{2-[(1R)-1-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]propyl}oxy)ethyl]phenyl}-2-methylpropanoate
수율 70%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

실험 절차

To diisopropylamine (0.45 mL, 3.23 mmol), a 2.69 M solution of n-butyl lithium in hexane (1.20 mL, 3.23 mmol) was added at −78° C. followed by stirring for 15 minutes. After adding anhydrous tetrahydrofuran (2 mL), the mixture was further stirred for 15 minutes at −78° C. Subsequently, a solution of methyl 3-{2-[(1R)-1-({(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]propyl}oxy)ethyl]phenyl}propanoate (615 mg, 1.08 mmol), which had been obtained in Example 179 (179a), in tetrahydrofuran (1 mL) was added thereto and stirred at −78° C. for 0.5 hours. After adding methyl iodide (0.6 mL, 6.46 mmol), the mixture was stirred at room temperature for 17 hours. Upon the completion of the reaction, water was added. After extracting the mixture with ethyl acetate, the solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (n-hexane/ethyl acetate=85/15) to give the title compound as a colorless oily substance (446 mg, yield 70%).

후처리

  1. stirringthe mixture was further stirred for 15 minutes at −78° C
  2. additionwas added
  3. stirringstirred at −78° C. for 0.5 hours
  4. stirringthe mixture was stirred at room temperature for 17 hours
  5. additionwas added
  6. extractionAfter extracting the mixture with ethyl acetate
  7. distillationthe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (n-hexane/ethyl acetate=85/15)

출처 및 근거

ORD 기록
ord-57b6afb13fd44d52bd49583d0edaddc8
출처 데이터셋
uspto-grants-2012_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08173631B2

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