Methanol → HCID 15044884, compound

HRID 846180Notes

Reaction equation

HRID 846180 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:36]=[CH:37][C:38]=1[O:39][CH3:40])[CH2:6][C@H:7]1[CH2:11][CH2:10][CH2:9][N:8]1[C:12](=O)[CH2:13][CH2:14][CH2:15][CH2:16][C:17]([N:19]1[CH2:23][CH2:22][CH2:21][C@@H:20]1[CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[C:27]([O:33][CH3:34])[CH:26]=1)=O.CO.Cl.CO>C1COCC1>[CH3:34][O:33][C:27]1[CH:26]=[C:25]([CH:30]=[CH:29][C:28]=1[O:31][CH3:32])[CH2:24][C@H:20]1[CH2:21][CH2:22][CH2:23][N:19]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13][CH2:12][N:8]1[CH2:9][CH2:10][CH2:11][C@@H:7]1[CH2:6][C:5]1[CH:36]=[CH:37][C:38]([O:39][CH3:40])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 15044883HCID 15044883, compoundHCID 21893726Hydrochloride methanol

Product 1

HCID 15044884HCID 15044884, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(R,R)-1,6-bis[2-(3,4-dimethoxybenzyl)pyrrolidin-1-yl]-1,6-dioxohexane (0.001 mol) in dry THF was added to a solution containing 0.5 mL (0.005 mol) 10M BH3 ·DMS, and the solution was heated under reflux in an argon atmosphere. Heating was maintained for 2 hours, after which time the mixture was cooled and 10 mL anhydrous methanol was added dropwise. After gas evolution had subsided, 10 mL of saturated HCl-MeOH was added dropwise and the mixture heated under reflux for 15 minutes. The mixture was cooled to room temperature and the solvent removed in vacuo, leaving an oily residue whose volume was further reduced by Kugelrohr distillation (100° C., 0.05 Torr). Finally, the residue was dissolved in isopropyl alcohol, and ether was added until the solution became cloudy. Crystallization occurred overnight, giving (R,R)-1,6-bis[2-(3,4-dimethoxybenzyl)pyrrolidin-1-yl]hexane.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux in an argon atmosphere
  3. temperatureHeating
  4. temperaturewas maintained for 2 hours
  5. temperatureafter which time the mixture was cooled
  6. temperaturethe mixture heated
  7. temperatureunder reflux for 15 minutes
  8. customthe solvent removed in vacuo
  9. customleaving an oily residue whose volume
  10. distillationwas further reduced by Kugelrohr distillation (100° C., 0.05 Torr)
  11. dissolutionFinally, the residue was dissolved in isopropyl alcohol
  12. additionether was added until the solution
  13. customCrystallization

Sources & evidence

ORD record
ord-b86a1a6bdaf2470ebbebf42e85a8acf3
Source dataset
uspto-grants-1992_08
Patent number
US05135944

Reaction notes

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