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

HRID 923448
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HRID 923448 반응식
[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
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 4

HCID 887MethanolHCID 24591Bismuth trichlorideHCID 4311764Sodium borohydrideHCID 59540376HCID 59540376, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 702
Ethanol
용매

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온도
0 °C

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-5eab25a08ced46e7975790ffc0cb89a5
출처 데이터셋
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09278922B2

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