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Methanol → 3-[6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-yl]-oxetan-3-ol

HRID 83181
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HRID 83181 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([O:8][CH2:9][C:10]2[C:11]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[N:12][O:13][C:14]=2[CH3:15])=[N:6][CH:7]=1.C([Li])CCC.[O:27]1[CH2:30][C:29](=[O:31])[CH2:28]1.CO>C1COCC1>[CH3:15][C:14]1[O:13][N:12]=[C:11]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]=1[CH2:9][O:8][C:5]1[N:6]=[CH:7][C:2]([C:29]2([OH:31])[CH2:30][O:27][CH2:28]2)=[CH:3][CH:4]=1
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참가 물질

6

반응물 4

HCID 887MethanolHCID 150242543-OxetanoneHCID 684448075-Bromo-2-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridineHCID 178418339Butyllithium

생성물 1

HCID 684438433-[6-(5-Methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridin-3-yl]-oxetan-3-ol수율 66.2%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매

실험 절차

A solution of 5-bromo-2-(5-methyl-3-phenyl-isoxazol-4-ylmethoxy)-pyridine (100 mg, 0.29 mmol) THF (3 mL) was treated with n-butyl lithium (1.6 M in hexanes, 0.18 mL, 0.29 mmol) at −75° C. Then a solution of 3-oxetanone (22.0 mg, 0.29 mmol) in THF (1 mL) was added and the mixture was stirred for 10 min. Methanol was then added and the mixture was allowed to warm to room temperature. Purification by chromatography (SiO2, ethylacetate/heptane 2:8 to 1:1) afforded the title compound (65 mg, 66%) as a white solid. MS: m/e=339.1 [M+H]+.

후처리

  1. customPurification by chromatography (SiO2, ethylacetate/heptane 2:8 to 1:1)

출처 및 근거

ORD 기록
ord-cc41d92784be4152963a76b9b1e98e5b
출처 데이터셋
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08846719B2

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