3,4-dihydro-2H-pyran → (2R)-1-morpholino-2-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-one

HRID 379656

반응식

HRID 379656 반응식
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[OH:7][C@H:8]([CH3:17])[C:9]([N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1)=[O:10].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>ClCCl>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:7][C@H:8]([CH3:17])[C:9]([N:11]1[CH2:12][CH2:13][O:14][CH2:15][CH2:16]1)=[O:10]

참가 물질

5

반응물 3

HCID 80803,4-dihydro-2H-pyranHCID 521998p-Toluenesulfonic acid monohydrateHCID 14978393(R)-2-Hydroxy-1-morpholinopropan-1-one

생성물 1

HCID 10977653(2R)-1-morpholino-2-((tetrahydro-2H-pyran-2-yl)oxy)propan-1-one수율 95%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

반응 조건

온도
0 °C

실험 절차

3,4-Dihydro-2H-pyran (90.5 ml, 1.2 eq) was added dropwise to a mixture of 4-[(R)-2-hydroxypropionyl]morpholine (132 g) and p-toluenesulfonic acid monohydrate (500 mg, 0.003 eq) in dry dichloromethane (500 ml) over a period of 15 min with stirring at 0° C. After being stirred for 30 min at 0° C., the mixture was washed with aqueous sodium bicarbonate, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Purification of the residue by silica gel chromatography, using n-hexane: ethyl acetate (8:1)˜ethyl acetate as an eluent, gave 4-[(2R)-2-(3,4,5,6-Tetrahydro-2H-pyran-2-yloxy)propionyl]morpholine (191.6 g, 95% yield) as a pale yellow oil.

후처리

  1. stirringAfter being stirred for 30 min at 0° C.
  2. washthe mixture was washed with aqueous sodium bicarbonate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPurification of the residue by silica gel chromatography

출처 및 근거

ORD 기록
ord-99c1990a46ee403da016a260d508eb23
출처 데이터셋
uspto-grants-2001_10
특허 번호
US06300353B1

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