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Methanol → (S,E)-tert-butyl 2-(4-(((4-aminobenzyl)(phenyl)amino)methyl)styryl)pyrrolidine-1-carboxylate

HRID 923448
ノート
印刷プレビュー

反応式

HRID 923448 の反応式
[N+:1]([C:4]1[CH:38]=[CH:37][C:7]([CH2:8][N:9]([CH2:16][C:17]2[CH:36]=[CH:35][C:20](/[CH:21]=[CH:22]/[C@@H:23]3[CH2:27][CH2:26][CH2:25][N:24]3[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:19][CH:18]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[CH:6][CH:5]=1)([O-])=O.[Bi](Cl)(Cl)Cl.[BH4-].[Na+].CO>C(O)C>[NH2:1][C:4]1[CH:38]=[CH:37][C:7]([CH2:8][N:9]([CH2:16][C:17]2[CH:36]=[CH:35][C:20](/[CH:21]=[CH:22]/[C@@H:23]3[CH2:27][CH2:26][CH2:25][N:24]3[C:28]([O:30][C:31]([CH3:33])([CH3:34])[CH3:32])=[O:29])=[CH:19][CH:18]=2)[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[CH:6][CH:5]=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

6

反応物 4

HCID 887MethanolHCID 24591Bismuth trichlorideHCID 4311764Sodium borohydrideHCID 59540376HCID 59540376、化合物

生成物 1

HCID 59540411(S,E)-tert-butyl 2-(4-(((4-aminobenzyl)(phenyl)amino)methyl)styryl)pyrrolidine-1-carboxylate

試薬・触媒・溶媒 1

HCID 702
Ethanol
溶媒

反応条件

温度
0 °C

実験手順

To a solution of the product of Example 149E (0.8 g, 1.56 mmol) dissolved in ethanol (20 mL) was cooled in an ice bath to 0° C., then bismuth(III) chloride (1.47 g, 4.67 mmol) was added followed by the portionwise addition of sodium borohydride (943 mg, 24.92 mmol) and warming the solution to room temperature for 20 minutes. The methanol was added and the solid removed by filtration, the filtrate concentrated to an oil, which was redissolved with dichloromethane and extracted with aqueous sodium bicarbonate. The organic solution was then dried, filtered, and concentrated to afford the title compound. m/z 484 (M+H)+.

後処理

  1. temperaturewarming the solution to room temperature for 20 minutes
  2. customthe solid removed by filtration
  3. concentrationthe filtrate concentrated to an oil, which
  4. dissolutionwas redissolved with dichloromethane
  5. extractionextracted with aqueous sodium bicarbonate
  6. customThe organic solution was then dried
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-5eab25a08ced46e7975790ffc0cb89a5
出典データセット
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09278922B2

反応ノート

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