Water → Methyl 3-{2-[(1R)-1-({(2R)-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]-2-hydroxypropyl}oxy)ethyl]phenyl}-2,2-dimethylpropanoate

HRID 1920795ノート

反応式

HRID 1920795 の反応式
[Si]([O:8][C@H:9]([CH2:28][N:29]1[CH2:33][CH2:32][CH2:31][C@H:30]1[CH2:34][C:35]1[CH:40]=[CH:39][C:38]([CH3:41])=[C:37]([F:42])[CH:36]=1)[CH2:10][O:11][C@@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23])[CH3:13])(C(C)(C)C)(C)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.O>C1COCC1>[F:42][C:37]1[CH:36]=[C:35]([CH:40]=[CH:39][C:38]=1[CH3:41])[CH2:34][C@@H:30]1[CH2:31][CH2:32][CH2:33][N:29]1[CH2:28][C@@H:9]([OH:8])[CH2:10][O:11][C@@H:12]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21]([CH3:27])([CH3:26])[C:22]([O:24][CH3:25])=[O:23])[CH3:13]

参加物

5

反応物 3

HCID 962WaterHCID 2724141Tetrabutylammonium Fluoride2 回HCID 58581066methyl 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}-2,2-dimethylpropanoate

生成物 1

HCID 58580852Methyl 3-{2-[(1R)-1-({(2R)-3-[(2S)-2-(3-fluoro-4-methylbenzyl)pyrrolidin-1-yl]-2-hydroxypropyl}oxy)ethyl]phenyl}-2,2-dimethylpropanoate収率 83%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

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}-2,2-dimethylpropanoate (308 mg, 0.51 mmol), which had been obtained in Example 179 (179c), in THF (3.1 mL) was added with 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (0.72 mL, 0.72 mmol), and stirred at room temperature. After stirring for 2 hours, a 1M solution of tetrabutylammonium fluoride in tetrahydrofuran (1.5 mL, 1.50 mmol) was added and further stirred for 48 hours. Upon the completion of the reaction, water (5 mL) was added and the mixture was extracted with ethyl acetate. The solvent was removed under reduced pressure. The residue was purified silica gel chromatography (n-hexane/ethyl acetate=3/7) to give the title compound as a pale yellow oily substance (206 mg, yield 83%).

後処理

  1. stirringAfter stirring for 2 hours
  2. stirringfurther stirred for 48 hours
  3. additionwas added
  4. extractionthe mixture was extracted with ethyl acetate
  5. customThe solvent was removed under reduced pressure
  6. customThe residue was purified silica gel chromatography (n-hexane/ethyl acetate=3/7)

出典と根拠

ORDレコード
ord-898ccdaee914456f8317b0dc8a880996
出典データセット
uspto-grants-2012_05
特許番号
US08173631B2

反応ノート

読み込み中…