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(R)-3-(1H-indol-3-yl)-N-(2-methoxybenzyl)-2-(N-triphenylmethylamino)propanamide → HCID 10554728, compound

HRID 850370
Notes
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Reaction equation

HRID 850370 reaction equation
COCCO[AlH2-]OCCOC.[Na+].[H-].COCCO[Al+]OCCOC.[Na+].[H-].[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([CH2:36][C@@H:37]([NH:50][C:51]([C:64]2[CH:69]=[CH:68][CH:67]=[CH:66][CH:65]=2)([C:58]2[CH:63]=[CH:62][CH:61]=[CH:60][CH:59]=2)[C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)[C:38]([NH:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[O:48][CH3:49])=O)=[CH:28]1>C1(C)C=CC=CC=1.O1CCCC1>[NH:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29]([CH2:36][C@@H:37]([NH:50][C:51]([C:64]2[CH:65]=[CH:66][CH:67]=[CH:68][CH:69]=2)([C:58]2[CH:59]=[CH:60][CH:61]=[CH:62][CH:63]=2)[C:52]2[CH:53]=[CH:54][CH:55]=[CH:56][CH:57]=2)[CH2:38][NH:40][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][C:43]=2[O:48][CH3:49])=[CH:28]1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 11801087(R)-3-(1H-indol-3-yl)-N-(2-methoxybenzyl)-2-(N-triphenylmethylamino)propanamideHCID 16684438Red-AlHCID 21584525Sodium bis(2-methoxyethoxy)aluminiumhydride

Product 1

HCID 10554728HCID 10554728, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent
HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

RED-AL™, [a 3.4 M, solution of sodium bis(2-methoxyethoxy)aluminum hydride in toluene] (535 ml, 1.819 mol), dissolved in anhydrous tetrahydrofuran (400 ml) was slowly added using an addition funnel to a refluxing solution of the acylation product, (R)-3-(1H-indol-3-yl)-N-(2-methoxybenzyl)-2-(N-triphenylmethylamino)propanamide (228.6 g, 0.404 mols) produced supra, in anhydrous tetrahydrofuran (1.0 L) under a nitrogen atmosphere. The reaction mixture became a purple solution. The reaction was quenched after at least 20 hours by the slow addition of excess saturated Rochelle's salt solution (potassium sodium tartrate tetrahydrate). The organic layer was isolated, washed with brine (2×), dried over anhydrous sodium sulfate, filtered, and concentrated to an oil on a rotary evaporator. No further purification was done and the product was used directly in the next step.

Workup

  1. additionwas slowly added
  2. customproduced supra
  3. customThe reaction was quenched after at least 20 hours by the slow addition of excess saturated Rochelle's salt solution (potassium sodium tartrate tetrahydrate)
  4. customThe organic layer was isolated
  5. washwashed with brine (2×)
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated to an oil on a rotary evaporator
  9. customNo further purification

Sources & evidence

ORD record
ord-092fd49fa4ee4808bf46f2c24bab7b0b
Source dataset
uspto-grants-2000_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06017930

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes