Triethylamine → tert-butyl 3-(5-(1-(2,4-dimethoxybenzylimino)butyl)-1-methyl-1H-indol-2-yl)pyrrolidine-1-carboxylate

HRID 1481734Notes

Reaction equation

HRID 1481734 reaction equation
[C:1]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[C:10]([CH:16]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])[CH2:17]1)=[CH:9]2)(=O)[CH2:2][CH2:3][CH3:4].[CH3:28][O:29][C:30]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:31]=1[CH2:32][NH2:33].CCN(CC)CC>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[CH3:28][O:29][C:30]1[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:31]=1[CH2:32][N:33]=[C:1]([C:6]1[CH:7]=[C:8]2[C:12](=[CH:13][CH:14]=1)[N:11]([CH3:15])[C:10]([CH:16]1[CH2:20][CH2:19][N:18]([C:21]([O:23][C:24]([CH3:25])([CH3:27])[CH3:26])=[O:22])[CH2:17]1)=[CH:9]2)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 5972502,4-DimethoxybenzylamineHCID 71284618tert-butyl 3-(5-butyryl-1-methyl-1H-indol-2-yl)pyrrolidine-1-carboxylate

Product 1

HCID 89421810tert-butyl 3-(5-(1-(2,4-dimethoxybenzylimino)butyl)-1-methyl-1H-indol-2-yl)pyrrolidine-1-carboxylate

Reagents, catalysts & solvents 2

HCID 24193Titanium TetrachlorideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To solution of tert-butyl 3-(5-butyryl-1-methyl-1H-indol-2-yl)pyrrolidine-1-carboxylate (0.823 g, 2.22 mmol) in DCM (5 mL) was added 2,4-dimethoxybenzylamine (0.38 mL, 2.53 mmol) and NEt3 (0.90 mL, 6.45 mmol). Mixture was cooled to 0° C. before TiCl4 solution (1M DCM, 1.45 mL, 1.45 mmol) was added dropwise via syringe pump over 30 min. Reaction was allowed to warm to room temperature and stirred overnight. Mixture was diluted with DCM (10 mL) and then quenched with NaHCO3 (aqueous saturated, 10 mL). Upon vigorous shaking organic phase was separated using a PTFE phase separator, dried over Na2SO4. Removal of the solvent afforded product (1.15 g, quant) as yellow oil, which was taken directly into next steps without purification.

Workup

  1. additionwas added dropwise via syringe pump over 30 min
  2. customReaction
  3. customquenched with NaHCO3 (aqueous saturated, 10 mL)
  4. customUpon vigorous shaking organic phase was separated
  5. dry with materialdried over Na2SO4
  6. customRemoval of the solvent
  7. customafforded product (1.15 g, quant) as yellow oil, which
  8. customwas taken directly into next steps without purification

Sources & evidence

ORD record
ord-a5d155fd4b82472c866b883f50c9b507
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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