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Hydrogen Peroxide → (S)-4-[(S)-1-(2,6-difluoropyridin-3-yl)ethyl]-2-hydroxy-6-methylmorpholin-3-one

HRID 16341
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HRID 16341 반응식
C([BH-](C(CC)C)C(CC)C)(CC)C.[Li+].[F:15][C:16]1[C:21]([C@@H:22]([N:24]2[CH2:29][C@H:28]([CH3:30])[O:27][C:26](=[O:31])[C:25]2=[O:32])[CH3:23])=[CH:20][CH:19]=[C:18]([F:33])[N:17]=1.[OH-].[Na+].OO.S([O-])(O)=O.[Na+]>C1(C)C=CC=CC=1.C1COCC1.C1COCC1>[F:15][C:16]1[C:21]([C@@H:22]([N:24]2[CH2:29][CH:28]([CH3:30])[O:27][C@H:26]([OH:31])[C:25]2=[O:32])[CH3:23])=[CH:20][CH:19]=[C:18]([F:33])[N:17]=1
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참가 물질

8

반응물 5

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 3611392Lithium tri-s-butylborohydrideHCID 23665763Sodium BisulfiteHCID 68717775(S)-4-[(S)-1-(2,6-difluoropyridin-3-yl)ethyl]-6-methylmorpholine-2,3-dione

생성물 1

HCID 68717852(S)-4-[(S)-1-(2,6-difluoropyridin-3-yl)ethyl]-2-hydroxy-6-methylmorpholin-3-one
수율 99.7%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 22635083Tetrahydrofuran toluene용매

실험 절차

A THF solution (20 mL) of 1 M lithium tri-s-butyl borohydride was dropwise added to a THF solution of (S)-4-[(S)-1-(2,6-difluoropyridin-3-yl)ethyl]-6-methylmorpholin-2,3-dione (4.5 g) at −50° C. or below. The resulting reaction solution was stirred for 2 hr. To the reaction solution, a 5 N sodium hydroxide aqueous solution (1.66 mL) and 30% hydrogen peroxide aqueous solution (6.78 mL) were added in this order at −10° C. or below. The resulting reaction solution was stirred for 1 hr, and then sodium hydrogensulfite (520 mg) was added thereto. The resulting reaction solution was stirred for 30 min, and then saturated saline and 50% toluene-THF were added thereto. The organic layer was separated, and the water layer was extracted with 50% toluene-THF. All the organic layers were combined and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1 to 0:1) to give 4.52 g of the title compound. The physical property values of this compound were as follows:

후처리

  1. customThe resulting reaction solution
  2. customThe resulting reaction solution
  3. stirringwas stirred for 1 hr
  4. customThe resulting reaction solution
  5. stirringwas stirred for 30 min
  6. customThe organic layer was separated
  7. extractionthe water layer was extracted with 50% toluene-THF
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (heptane:ethyl acetate=1:1 to 0:1)

출처 및 근거

ORD 기록
ord-e4add3c7b0cb46f892e2e022b2640d7e
출처 데이터셋
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07737141B2

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