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

HRID 2354114노트

반응식

HRID 2354114 반응식
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]

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-af77196465894af68a3439b45ebb000f
출처 데이터셋
uspto-grants-2010_07
특허 번호
US07750167B2

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