Hydrochloric Acid → (R)-1-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-phenyl-4-carboxypiperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine

HRID 1601449Notes

Reaction equation

HRID 1601449 reaction equation
[C:1]1([C:7]2([C:28]([OH:30])=[O:29])[CH2:12][CH2:11][N:10]([CH2:13][CH2:14][C@:15]3([C:20]4[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=4)[CH2:19][CH2:18][NH:17][CH2:16]3)[CH2:9][CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)(O)[O-].[Na+].[CH3:36][O:37][C:38]1[CH:39]=[C:40]([CH:44]=[C:45]([O:49][CH3:50])[C:46]=1[O:47][CH3:48])[C:41](Cl)=[O:42].Cl>O1CCCC1.O>[CH3:50][O:49][C:45]1[CH:44]=[C:40]([CH:39]=[C:38]([O:37][CH3:36])[C:46]=1[O:47][CH3:48])[C:41]([N:17]1[CH2:18][CH2:19][C@:15]([CH2:14][CH2:13][N:10]2[CH2:11][CH2:12][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)([C:28]([OH:30])=[O:29])[CH2:8][CH2:9]2)([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[C:22]([Cl:27])[CH:21]=2)[CH2:16]1)=[O:42]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 78282Benzoyl chloride, 3,4,5-trimethoxy-HCID 516892Sodium BicarbonateHCID 53783991(S)-3-(2-(4-phenyl-4-carboxypiperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine

Product 1

HCID 53652197(R)-1-(3,4,5-Trimethoxybenzoyl)-3-(2-(4-phenyl-4-carboxypiperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent2×

Procedure

Combine (S)-3-(2-(4-phenyl-4-carboxypiperidin-1-yl)ethyl)-3-(3,4-dichlorophenyl)pyrrolidine (50 g, 112 mmol) and sodium bicarbonate (30 g) in tetrahydrofuran (1300 mL) and water (300 mL). Add portionwise over about 45 minutes, a solution of 3,4,5-trimethoxybenzoyl chloride (26 g, 112 mmol) in tetrahydrofuran (130 mL). After 2 hours, dilute with water (1000 mL). Adjust the pH to about 4 using concentrated aqueous hydrochloric acid to give a solid. Collect the solid by filtration and rinse with water. Triturate the solid with methanol (1300 mL) and water (1300 mL). Filter, rinse with water and dry in vacuo to give the title compound.

Workup

  1. additionAdd portionwise over about 45 minutes
  2. customto give a solid
  3. customCollect the solid
  4. filtrationby filtration
  5. washrinse with water
  6. customTriturate the solid with methanol (1300 mL) and water (1300 mL)
  7. filtrationFilter
  8. washrinse with water
  9. customdry in vacuo

Sources & evidence

ORD record
ord-20ce7c95e6a04f91ba682995298b5855
Source dataset
uspto-grants-1999_11
Patent number
US05977139

Reaction notes

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