Water → tert-Butyl (2-diethylaminoethyl)-[(R)-1-(4-nitrophenyl)pyrrolidin-3-yl]carbamate

HRID 1354770Notes

Reaction equation

HRID 1354770 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([N:10]2[CH2:14][CH2:13][C@@H:12]([NH:15][C:16](=[O:22])[O:17][C:18]([CH3:21])([CH3:20])[CH3:19])[CH2:11]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[H-].[Na+].Cl.Cl[CH2:27][CH2:28][N:29]([CH2:32][CH3:33])[CH2:30][CH3:31].O>CN(C)C=O>[CH2:28]([N:29]([CH2:32][CH3:33])[CH2:30][CH2:31][N:15]([C@@H:12]1[CH2:13][CH2:14][N:10]([C:7]2[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][CH:8]=2)[CH2:11]1)[C:16](=[O:22])[O:17][C:18]([CH3:19])([CH3:21])[CH3:20])[CH3:27]

Participants

6

Reactant 4

HCID 962WaterHCID 133631-Chloro-2-(diethylamine)ethane hydrochlorideHCID 24758Sodium hydrideHCID 86594863tert-butyl [(3R)-1-(4-nitrophenyl)pyrrolidin-3-yl]carbamate

Product 1

HCID 86594886tert-Butyl (2-diethylaminoethyl)-[(R)-1-(4-nitrophenyl)pyrrolidin-3-yl]carbamate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl [(R)-1-(4-nitrophenyl)pyrrolidin-3-yl]carbamate (6.0 g) was dissolved in 50 ml of N,N-dimethylformamide and, after addition of sodium hydride (1.1 g), stirred at room temperature for 30 minutes, and subsequently chlorethyldiethylamine hydrochloride (4.1 g) was added. The mixture was subsequently stirred at room temperature with exclusion of moisture for 4 hours. The reaction was stopped by adding water (50 ml), and this was followed by extraction with ethyl acetate (3×50 ml) and drying of the combined organic phases over magnesium sulfate, and removal of the solvent. This resulted in the product with the molecular weight of 406.53 (C21H34N4O4); MS (ESI): 407 (M+H+).

Workup

  1. stirringThe mixture was subsequently stirred at room temperature with exclusion of moisture for 4 hours
  2. extractionthis was followed by extraction with ethyl acetate (3×50 ml)
  3. dry with materialdrying of the combined organic phases over magnesium sulfate, and removal of the solvent
  4. customThis resulted in the product with the molecular weight of 406.53 (C21H34N4O4)

Sources & evidence

ORD record
ord-98ebe16f96144f9c9174e5ca28cd7ac1
Source dataset
uspto-grants-2007_05
Patent number
US07223788B2

Reaction notes

Loading…