Hydrochloric Acid → trans-n-Methyl-2-(2-hydroxyphenyl)-3-(2-bromo-5-chlorophenyl)-pyrrolidine

HRID 2354114Notes

Reaction equation

HRID 2354114 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1/[CH:11]=[CH:12]/[C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[Br:20])(=O)C.F[C:22](F)(F)[C:23](O)=O.CO[CH2:30][N:31]([Si](C)(C)C)C.[OH-].[K+].Cl>C1(C)C=CC=CC=1.O>[CH3:30][N:31]1[CH2:23][CH2:22][C@@H:12]([C:13]2[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=2[Br:20])[C@@H:11]1[C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[OH:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 14797Potassium HydroxideHCID 593812282-[(E)-2-(2-Bromo-5-chlorophenyl)ethenyl]phenyl acetateHCID 86617526HCID 86617526, compound

Product 1

HCID 68506394trans-n-Methyl-2-(2-hydroxyphenyl)-3-(2-bromo-5-chlorophenyl)-pyrrolidine

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Procedure

trans-2-Acetoxy-2′-bromo-5′-chlorostilbene (1189 g, 3381 mmol) was dissolved in toluene (5350 ml) and trifluoroacetic acid (10.42 ml, 165 mmol) at 33° C. N-methoxymethyl-N-trimethylsilyl-N-methylamine (670 g, 4153 mmol) was added in the course of 1 hour. The organic layer was concentrated under vacuum to an oil. This oil was dissolved in methanol (4160 ml) at 30° C. Potassium hydroxide (209 g, 3725 mmol) in water (900 ml) was added. After 30 minutes, the pH was adjusted to 8-9 with 3N HCl (approx. 200 ml). The mixture was stirred for 30 minutes and filtered. The product was dried for 24h under vacuum, yielding the title pyrrolidine in 1188 grams (96%). Purity according to HPLC is >99,0% a/a.

Workup

  1. customat 33° C
  2. concentrationThe organic layer was concentrated under vacuum to an oil
  3. dissolutionThis oil was dissolved in methanol (4160 ml) at 30° C
  4. filtrationfiltered
  5. dry with materialThe product was dried for 24h under vacuum

Sources & evidence

ORD record
ord-af77196465894af68a3439b45ebb000f
Source dataset
uspto-grants-2010_07
Patent number
US07750167B2

Reaction notes

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