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Ethanol → tert-Butyl (3R,5S)-3-(hydroxymethyl)-5-[{[1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl)(2-methylpropyl)amino]piperidine-1-carboxylate

HRID 1259930
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HRID 1259930 반응식
[BH4-].[Na+].C(O)C.[Cl-].[Ca+2].[Cl-].[CH3:9][O:10][CH2:11][CH2:12][CH2:13][CH2:14][N:15]1[C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=2[N:17]=[C:16]1[C:24]([N:26]([CH2:44][CH:45]([CH3:47])[CH3:46])[C@@H:27]1[CH2:32][N:31]([C:33]([O:35][C:36]([CH3:39])([CH3:38])[CH3:37])=[O:34])[CH2:30][C@H:29]([C:40](OC)=[O:41])[CH2:28]1)=[O:25]>C1COCC1.O.C(OCC)(=O)C>[OH:41][CH2:40][C@@H:29]1[CH2:28][C@H:27]([N:26]([C:24]([C:16]2[N:15]([CH2:14][CH2:13][CH2:12][CH2:11][O:10][CH3:9])[C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=3[N:17]=2)=[O:25])[CH2:44][CH:45]([CH3:47])[CH3:46])[CH2:32][N:31]([C:33]([O:35][C:36]([CH3:38])([CH3:37])[CH3:39])=[O:34])[CH2:30]1
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참가 물질

8

반응물 4

HCID 702EthanolHCID 4311764Sodium borohydrideHCID 5284359Calcium ChlorideHCID 583555501-tert-Butyl 3-methyl(3R,5S)-5-[{[1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-1,3-dicarboxylate

생성물 1

HCID 58355672tert-Butyl (3R,5S)-3-(hydroxymethyl)-5-[{[1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl)(2-methylpropyl)amino]piperidine-1-carboxylate
수율 47.4%

시약·촉매·용매 3

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

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온도
0 °C

실험 절차

Sodium borohydride (4.45 g) was suspended in THF (25 ml)-ethanol (75 ml), and calcium chloride (6.5 g) was added. After stirring at 0° C. for 1 hr, a solution of 1-tert-butyl 3-methyl (3R,5S)-5-[{[1-(4-methoxybutyl)-1H-benzimidazol-2-yl]carbonyl}(2-methylpropyl)amino]piperidine-1,3-dicarboxylate (4.0 g) in THF (50 ml) was added. After stirring at room temperature for 12 hr, ethyl acetate (150 ml) and water (50 ml) were slowly added in this order, and the mixture was filtered. The organic layer of the filtrate was partitioned, washed with brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The residue was dried under reduced pressure to give the object product (1.8 g).

후처리

  1. additionwas added
  2. stirringAfter stirring at room temperature for 12 hr
  3. filtrationthe mixture was filtered
  4. customThe organic layer of the filtrate was partitioned
  5. washwashed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customThe residue was dried under reduced pressure

출처 및 근거

ORD 기록
ord-01bf91ab3910473e86b4e00a0edade99
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08466282B2

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