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

HRID 923448
Notes
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Reaction equation

HRID 923448 reaction equation
[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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702
Ethanol
Solvent

Conditions

Temperature
0 °C

Procedure

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)+.

Workup

  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

Sources & evidence

ORD record
ord-5eab25a08ced46e7975790ffc0cb89a5
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09278922B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes