Peracetic Acid → tert-Butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

HRID 1666409노트

반응식

HRID 1666409 반응식
CC1(C)C(C)(C)OB([C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:17]=[C:18]([CH:33]=[CH:34][CH:35]=3)[CH:19]=[C:20]3[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]3)=[N:13][CH:14]=2)O1.C(OO)(C)=[O:38]>C1COCC1>[OH:38][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:17]=[C:18]([CH:33]=[CH:34][CH:35]=2)[CH:19]=[C:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:30])([CH3:31])[CH3:32])=[O:27])[CH2:24][CH2:25]2)=[N:13][CH:14]=1

참가 물질

4

반응물 2

HCID 6585Peracetic AcidHCID 66875728Tert-butyl 4-(3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate

생성물 1

HCID 66875736tert-Butyl 4-(3-(5-hydroxypyridin-2-yloxy)benzylidene)piperidine-1-carboxylate수율 75.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of tert-butyl 4-(3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yloxy)benzylidene)piperidine-1-carboxylate (3.45 g, 7 mmol) in THF (15 mL) was added AcOOH (4.6 mL, 60.67 mmol) at 0° C. The temperature was allowed to warm to RT and the reaction was stirred for 3 h. The reaction was quenched with Na2SO3 solution at 0° C. and the pH of the solution was adjusted to 7-7.5. Then the mixture was extracted with ethyl acetate and the organic layer was dried over Na2SO4 and concentrated to dryness. The residue was purified by silica gel column chromatography (1:3 acetone:hexane) to give the title compound (2.02 g, 75%). 1H NMR (500 MHz, DMSO-d6): δ 9.67 (s, 1H), 7.72 (s, 1H), 7.28 (m, 2H), 6.98 (d, J=7.2 Hz, 1H), 6.89 (d, J=8.5 Hz, 1H), 6.85 (d, J=7.5 Hz), 6.83 (s, 1H), 6.35 (s, 1H), 3.41 (m, 2H), 3.31 (m, 2H), 2.38 (m, 2H), 2.27 (m, 2H), 1.41 (s, 9H); m/z (383.1, M+ H+).

후처리

  1. customThe reaction was quenched with Na2SO3 solution at 0° C.
  2. extractionThen the mixture was extracted with ethyl acetate
  3. dry with materialthe organic layer was dried over Na2SO4
  4. concentrationconcentrated to dryness
  5. customThe residue was purified by silica gel column chromatography (1:3 acetone:hexane)

출처 및 근거

ORD 기록
ord-ffc9df7cb4d44879a82c4a930541c700
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08044052B2

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