Ammonia → benzyl 4-[3-(2-hydroxyethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylate

HRID 2366548노트

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HRID 2366548 반응식
C([O:5][C:6]([CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)=[O:22])[CH2:17][CH2:16]2)[C:10]1=[O:31])=O)(C)(C)C.[BH4-].[Li+].N>C1COCC1>[OH:5][CH2:6][CH2:8][N:9]1[CH2:14][CH2:13][CH2:12][N:11]([CH:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)=[O:22])[CH2:17][CH2:16]2)[C:10]1=[O:31]

참가 물질

5

반응물 3

HCID 222AmmoniaHCID 4148881Lithium borohydrideHCID 68417510benzyl 4-[3-(tert-butoxycarbonylmethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylate

생성물 1

HCID 68420920benzyl 4-[3-(2-hydroxyethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylate수율 99.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of benzyl 4-[3-(tert-butoxycarbonylmethyl)-2-oxotetrahydropyrimidin-1(2H)-yl]piperidin-1-carboxylate (0.60 g) obtained in Example 35a) and lithium borohydride (0.091 g) in THF (15 mL) was refluxed for 5 hours. The reaction mixture was allowed to stand at room temperature and poured into an aqueous saturated ammonia solution under ice-cooling. The organic layer was separated, and the aqueous layer was extracted with dichloromethane. The organic layers were combined, washed with a saturated saline solution, dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=95/5) to obtain the title compound (0.50 g, 99%) as a colorless oil.

후처리

  1. customto stand at room temperature
  2. temperaturecooling
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with dichloromethane
  5. washwashed with a saturated saline solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (ethyl acetate to ethyl acetate/methanol=95/5)

출처 및 근거

ORD 기록
ord-902ed7ca9c6d4cd097bce5ffccb4e5fc
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08697865B2

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