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Sodium Azide → cis-4-Azido-2-benzhydryl-tetrahydropyran

HRID 606965
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HRID 606965 반응식
[CH:1]([C@H:14]1[CH2:19][C@H:18](OS(C)(=O)=O)[CH2:17][CH2:16][O:15]1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N-:25]=[N+:26]=[N-:27].[Na+]>CN(C=O)C.C(OCC)C>[N:25]([C@H:18]1[CH2:17][CH2:16][O:15][C@@H:14]([CH:1]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH2:19]1)=[N+:26]=[N-:27]
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참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 86605343methanesulfonic acid Trans-2-benzhydryl-tetrahydropyran-4-yl ester

생성물 1

HCID 86605345cis-4-Azido-2-benzhydryl-tetrahydropyran수율 82.7%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

Into a solution of trans-2-diphenylmethylpyran-4-yl methanesulfonate 4a (0.33 g, 0.95 mmol) in dry DMF (40 ml) was added sodium azide (0.18 g, 2.85 mmol). The mixture was heated to 100° C. and stirred for 4 hr. The mixture was diluted with ethyl ether, washed with 2M aqueous NaHCO3 and brine, and then dried over anhydrous Na2SO4. Removal of the solvent and purification by flash chromatography (Hexane/Ethyl Acetate 9:1) afforded compound 5a (0.23 g, 82.7% yield) as a liquid.

후처리

  1. washwashed with 2M aqueous NaHCO3 and brine
  2. dry with materialdried over anhydrous Na2SO4
  3. customRemoval of the solvent and purification by flash chromatography (Hexane/Ethyl Acetate 9:1)

출처 및 근거

ORD 기록
ord-3811e4eca6b3450c9017cf9568d21f7a
출처 데이터셋
uspto-grants-2011_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07915433B2

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