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

HRID 1666409ノート

反応式

HRID 1666409 の反応式
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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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+).

後処理

  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)

出典と根拠

ORDレコード
ord-ffc9df7cb4d44879a82c4a930541c700
出典データセット
uspto-grants-2011_10
特許番号
US08044052B2

反応ノート

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