Water → N-(5'-((3,3-Difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide

HRID 1468074ノート

反応式

HRID 1468074 の反応式
[F:1][C:2]1([F:25])[CH2:5][CH:4]([CH2:6][O:7][C:8]2[CH:16]=[C:15]3[C:11]([CH2:12][C:13]4([CH2:22][CH2:21][CH:20]([O:23][CH3:24])[CH2:19][CH2:18]4)[C:14]3=O)=[CH:10][CH:9]=2)[CH2:3]1.[CH3:26][C:27]([S:30]([NH2:32])=[O:31])([CH3:29])[CH3:28].O>C(OCC)(=O)C.C(O[Ti](OCC)(OCC)OCC)C>[F:25][C:2]1([F:1])[CH2:5][CH:4]([CH2:6][O:7][C:8]2[CH:16]=[C:15]3[C:11](=[CH:10][CH:9]=2)[CH2:12][C:13]2([CH2:18][CH2:19][CH:20]([O:23][CH3:24])[CH2:21][CH2:22]2)[C:14]3=[N:32][S:30]([C:27]([CH3:29])([CH3:28])[CH3:26])=[O:31])[CH2:3]1

参加物

6

反応物 3

HCID 962WaterHCID 3382465Tert-ButanesulfinamideHCID 867067216'-((3,3-Difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2'-inden]-1'(3'H)-one2 回

生成物 1

HCID 86706722N-(5'-((3,3-Difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2'-indene]-3'(1'H)-ylidene)-2-methylpropane-2-sulfinamide収率 31.3%

試薬・触媒・溶媒 2

HCID 178477244HCID 178477244、化合物触媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
80 °C

実験手順

6′-((3,3-Difluorocyclobutyl)methoxy)-4-methoxyspiro[cyclohexane-1,2′-inden]-1′(3′H)-one (Intermediate 14, 1.85 g, 5.28 mmol) and 2-methylpropane-2-sulfinamide (1.15 g, 9.50 mmol) were dissolved in 2-Me THF (40 mL). Tetraethoxytitanium (2.21 mL, 10.6 mmol) was added and the resulting mixture was heated to 80° C. over a weekend. The reaction mixture was cooled to r.t., and diluted with ethyl acetate (85 mL). Water (3 mL) was added under vigorous stirring and then the mixture was allowed to stand for 1 h. The mixture was filtered, the solvent was evaporated and the residue was purified by column chromatography on silica using a gradient of 0-70% ethyl acetate in heptanes. The product was recrystallized twice from EtOH. to give 0.750 g of the title compound (31% yield). MS (ES+) m/z 454 [M+H]+.

後処理

  1. temperatureThe reaction mixture was cooled to r.t.
  2. filtrationThe mixture was filtered
  3. customthe solvent was evaporated
  4. customthe residue was purified by column chromatography on silica using a gradient of 0-70% ethyl acetate in heptanes
  5. customThe product was recrystallized twice from EtOH

出典と根拠

ORDレコード
ord-7cd20821c2bc4d598944eaa3eb2446aa
出典データセット
uspto-grants-2015_04
特許番号
US09000185B2

反応ノート

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