Nitrogen → tert-Butyl 4-hydroxy-1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

HRID 1501803ノート

反応式

HRID 1501803 の反応式
[OH:1][CH:2]1[C:6]2([CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]2)[C:5](=[O:19])[NH:4][CH2:3]1.Br[C:21]1[CH2:25][O:24][C:23](=[O:26])[CH:22]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.C([O-])([O-])=O.[K+].[K+].N#N.O>CC([O-])=O.CC([O-])=O.[Pd+2].O1CCOCC1>[OH:1][CH:2]1[C:6]2([CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:18])[CH3:17])=[O:13])[CH2:10][CH2:11]2)[C:5](=[O:19])[N:4]([C:21]2[CH2:25][O:24][C:23](=[O:26])[CH:22]=2)[CH2:3]1

参加物

9

反応物 6

HCID 947NitrogenHCID 962WaterHCID 11430Potassium CarbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 117895364-bromo-5H-furan-2-oneHCID 86709491tert-Butyl 4-hydroxy-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate

生成物 1

HCID 86709498tert-Butyl 4-hydroxy-1-oxo-2-(5-oxo-2,5-dihydrofuran-3-yl)-2,8-diazaspiro[4.5]decane-8-carboxylate

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

To a round bottom flask was charged tert-butyl 4-hydroxy-1-oxo-2,8-diazaspiro[4.5]decane-8-carboxylate (300 mg, 1.11 mmol), 4-bromofuran-2(5H)-one (271 mg, 1.66 mmol), Pd(OAc)2 (24.9 mg, 0.111 mmol), Xantphos (96 mg, 0.166 mmol), and K2CO3 (307 mg, 2.22 mmol). The flask was sealed, vacuumed and back filled with N2 and filled with dioxane (4.5 mL) and H2O (60.0 μL, 3.33 mmol). The reaction mixture was heated at 90° C. overnight, then filtered through CELITE®, and evaporated to give the crude product, which was purified by column chromatography (0-10% MeOH/DCM) to give the title compound. LC/MS: [(M+1)]+=353

後処理

  1. customThe flask was sealed
  2. filtrationfiltered through CELITE®
  3. customevaporated
  4. customto give the crude product, which
  5. customwas purified by column chromatography (0-10% MeOH/DCM)

出典と根拠

ORDレコード
ord-ecff971837fc4df1aadb402fd5445c62
出典データセット
uspto-grants-2015_12
特許番号
US09206198B2

反応ノート

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