Sulfuric acid magnesium salt (1:1) → HCID 69585595, compound

HRID 1828161Notes

Reaction equation

HRID 1828161 reaction equation
[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([NH2:13])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:14]([N:16]1[C:20]2[CH:21]=[CH:22][C:23]([CH:25]=O)=[CH:24][C:19]=2[N:18]([CH2:27][CH3:28])[C:17]1=[O:29])[CH3:15].S([O-])([O-])(=O)=O.[Mg+2]>ClCCl>[CH2:1]([N:8]1[CH2:12][CH2:11][C@@H:10]([N:13]=[CH:25][C:23]2[CH:22]=[CH:21][C:20]3[N:16]([CH2:14][CH3:15])[C:17](=[O:29])[N:18]([CH2:27][CH3:28])[C:19]=3[CH:24]=2)[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 1519354(3R)-1-benzylpyrrolidin-3-amineHCID 6484105HCID 6484105, compound

Product 1

HCID 69585595HCID 69585595, compoundYield 103.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
22 °C

Procedure

To a dry flask charged with a stir bar was added (3R)-(−)-1-benzyl-3-aminopyrrolidine (202 mg, 1.15 mmoles) (commercial from TCI-US), 1,3-Diethyl-2-oxo-2,3-dihydro-1H-benzoimidazole-5-carbaldehyde (250 mg, 1.15 mmoles), magnesium sulfate (500 mg) and 5 ml of dichloromethane (0.23 M). The flask was sealed with a plastic cap and the resulting mixture was stirred for 20 hours at 22° C. The mixture was filtered through a nylon disk via syringes, rinsing with dichloromethane and the yellow filtrate was concentrated to give 450 mg of the title compound as a yellow gum/foam.

Workup

  1. additionTo a dry flask charged with a stir bar
  2. customThe flask was sealed with
  3. customa plastic cap
  4. filtrationThe mixture was filtered through a nylon disk via syringes
  5. washrinsing with dichloromethane
  6. concentrationthe yellow filtrate was concentrated

Sources & evidence

ORD record
ord-1620fae11d1f40c5b5488a0bb454c8ee
Source dataset
uspto-grants-2006_06
Patent number
US07056918B2

Reaction notes

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