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Triethylamine → Methyl 1-[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]-4-[3-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)propyl]piperidine-3-carboxylate

HRID 255292
ノート
印刷プレビュー

反応式

HRID 255292 の反応式
FC(F)(F)C(O)=O.[C:8]([C:10]1[CH:11]=[CH:12][C:13]2[O:18][CH2:17][C:16](=[O:19])[N:15]([CH2:20][CH2:21][CH2:22][CH:23]3[CH2:28][CH2:27][NH:26][CH2:25][CH:24]3[C:29]([O:31][CH3:32])=[O:30])[C:14]=2[CH:33]=1)#[N:9].[F:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=1/[CH:42]=[CH:43]/[CH:44]=O.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)(Cl)Cl.CO.C(OCC)(=O)C.O>[F:34][C:35]1[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=1/[CH:42]=[CH:43]/[CH2:44][N:26]1[CH2:27][CH2:28][CH:23]([CH2:22][CH2:21][CH2:20][N:15]2[C:14]3[CH:33]=[C:10]([C:8]#[N:9])[CH:11]=[CH:12][C:13]=3[O:18][CH2:17][C:16]2=[O:19])[CH:24]([C:29]([O:31][CH3:32])=[O:30])[CH2:25]1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 66774489methyl 4-[3-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)propyl]piperidine-3-carboxylate trifluoroacetate2 回HCID 86642138(2E)-3-(2,5-difluorophenyl)-2-propenal

生成物 1

HCID 15982403Methyl 1-[(2E)-3-(2,5-difluorophenyl)prop-2-en-1-yl]-4-[3-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)propyl]piperidine-3-carboxylate
収率 32.3%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒HCID 21584188Chloroform methanol溶媒

反応条件

温度
0 °C

実験手順

A solution of methyl 4-[3-(6-cyano-3-oxo-2,3-dihydro-4H-1,4-benzoxazin-4-yl)propyl]piperidine-3-carboxylate trifluoroacetate (Intermediate 130, crude, 171, 0.48 mmol), (2E)-3-(2,5-difluorophenyl)acrylaldehyde [FR 2872164] (81 mg, 0.48 mmol), and triethylamine (0.13 mL. 0.96 mmol) in chloroform/methanol (6 mL, 10:1) was heated over 3 Å molecular sieves at 70° C. for 3 hours. The reaction mixture was cooled to 0° C., and sodium triacetoxy borohydride (200 mg, 0.94 mmol) was added. The resulting reaction mixture was allowed to warm to room temperature and stir for 18 hours. The reaction was diluted with ethyl acetate (25 mL) and water (10 mL). The aqueous phase was separated and washed twice with ethyl acetate. The organic layers were combined, dried over magnesium sulfate and evaporated at reduced pressure. Chromatography on silica gel with diethyl ether gave the title compound as a off-white foam, (79 mg, 32%).

後処理

  1. customThe resulting reaction mixture
  2. temperatureto warm to room temperature
  3. customThe aqueous phase was separated
  4. washwashed twice with ethyl acetate
  5. dry with materialdried over magnesium sulfate
  6. customevaporated at reduced pressure

出典と根拠

ORDレコード
ord-2feeb24140a443faa3b7acbb16cd6a45
出典データセット
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07875715B2

反応ノート

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