Methanol → HCID 15044884, compound

HRID 2372834Notes

Reaction equation

HRID 2372834 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.CSC.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 887Methanol2×HCID 1068Dimethyl SulfideHCID 15044883HCID 15044883, compound

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

Sources & evidence

ORD record
ord-1cd48978c28f44bbb1db3e43d7b92e75
Source dataset
uspto-grants-1992_03
Patent number
US05100912

Reaction notes

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