(-)-Pseudoephedrine → HCID 9884032, compound

HRID 1648497Notes

Reaction equation

HRID 1648497 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].[CH3:10][C@@H:11]([NH:20][CH3:21])[C@H:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][CH:7]=[CH:6][C:3]=1[C@@H:4]1[N:20]([CH3:21])[C@H:11]([CH3:10])[C@@H:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[O:5]1

Participants

4

Reactant 2

HCID 62946(-)-PseudoephedrineHCID 811292-Bromobenzaldehyde

Product 1

HCID 9884032HCID 9884032, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

To a solution of 2-bromobenzaldehyde (18.78 g, 101.50 mmole, 1.0 eq) in toluene (100 mL) was added (-)-pseudoephedrine (16.73 g, 101.24 mmole, 1.0 eq). The mixture was refluxed for 16 h under an argon atmosphere using a Dean-Stark trap to remove the generated water. Concentration in vacuo gave 33.53 g (100%, corrected for 2 wt % toluene by 1H NMR) of a 40:1 mixture of title compound and a minor diastereomer as a light yellow oil.

Workup

  1. temperatureThe mixture was refluxed for 16 h under an argon atmosphere
  2. customto remove the generated water
  3. concentrationConcentration in vacuo
  4. customgave

Sources & evidence

ORD record
ord-003a1297be3b4da8971fb3b58b4d1ec4
Source dataset
uspto-grants-1995_07
Patent number
US05436347

Reaction notes

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