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

HRID 1516875Notes

Reaction equation

HRID 1516875 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 24 h 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. customThe product was dried for 24 h under vacuum

Sources & evidence

ORD record
ord-3734ace7618448d2a1c2f58ac2175e9d
Source dataset
uspto-grants-2012_07
Patent number
US08227623B2

Reaction notes

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