Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → 1,2-dibenzyl 3-tert-butyl (2S,3S)-5-(2-methoxy-2-oxoethylidene)piperidine-1,2,3-tricarboxylate

HRID 61427

反応式

HRID 61427 の反応式
[CH3:1][O:2][C:3](=[O:24])[CH:4]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O=[C:26]1[CH2:31][N:30]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[C@H:29]([C:42]([O:44][CH2:45][C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)=[O:43])[C@@H:28]([C:52]([O:54][C:55]([CH3:58])([CH3:57])[CH3:56])=[O:53])[CH2:27]1>C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:24])[CH:4]=[C:26]1[CH2:31][N:30]([C:32]([O:34][CH2:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[O:33])[C@H:29]([C:42]([O:44][CH2:45][C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)=[O:43])[C@@H:28]([C:52]([O:54][C:55]([CH3:56])([CH3:57])[CH3:58])=[O:53])[CH2:27]1

参加物

4

反応物 2

HCID 17453Acetic acid, 2-(triphenylphosphoranylidene)-, methyl esterHCID 593051041,2-Dibenzyl 3-(tert-butyl) (2S,3S)-5-oxopiperidine-1,2,3-tricarboxylate

生成物 1

HCID 866214861,2-dibenzyl 3-tert-butyl (2S,3S)-5-(2-methoxy-2-oxoethylidene)piperidine-1,2,3-tricarboxylate収率 80%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒2 回

実験手順

To an oven-dried 25 mL round-bottomed flask equipped with a magnetic stir bar and under a nitrogen gas atmosphere was placed methyl(triphenylphosphoranylidene)acetate (199 mg, 0.597 mmol) and toluene (5 mL). To this heterogeneous solution was added a solution of 1,2-dibenzyl 3-tert-butyl(2S,3S)-5-oxopiperidine-1,2,3-tricarboxylate (93 mg, 0.199 mmol) in toluene (3 mL). The reaction mixture was heated to reflux and stirred overnight. The volatiles were then removed in-vacuo and the yellow oil was purified by Combiflash (10 to 30% ethyl acetate in hexanes) to afford 83 mg (80%) of 1,2-dibenzyl 3-tert-butyl(2S,3S)-5-(2-methoxy-2-oxoethylidene)piperidine-1,2,3-tricarboxylate. LCMS (ESI): 424 (M-CO2t-Bu+2H+), 468 (M-t-Bu+2H+), 524 (M+H+).

後処理

  1. customTo an oven-dried 25 mL round-bottomed flask equipped with a magnetic stir bar and under a nitrogen gas atmosphere
  2. temperatureThe reaction mixture was heated
  3. temperatureto reflux
  4. customThe volatiles were then removed in-vacuo
  5. customthe yellow oil was purified by Combiflash (10 to 30% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-bae75d4a6891464a8177acd553e9ae94
出典データセット
uspto-grants-2016_09
特許番号
US09440958B2

関連ノート

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