Hydrochloric Acid → Hydrochloric Acid

HRID 1427726Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1427726
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([C@H:13]([O:20][C:21]2[CH:26]=[C:25]([Cl:27])[CH:24]=[C:23]([Cl:28])[CH:22]=2)[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH2:9]1)=O)(C)(C)C.CCO.Cl.C([Cl:36])(=O)C>>[Cl:28][C:23]1[CH:22]=[C:21]([CH:26]=[C:25]([Cl:27])[CH:24]=1)[O:20][C@H:13]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C@@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1.[ClH:36]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 6367Acetyl chlorideHCID 66924546(R)-3-[(S)-(3,5-dichlorophenoxy)phenylmethyl]pyrrolidine-1-carboxylic acid t-butyl ester

Produkt 2

HCID 313Hydrochloric AcidAusbeute 870 %HCID 44625571(R)-3-[(S)-(3,5-dichlorophenoxy)phenylmethyl]pyrrolidine

Versuchsvorschrift

(R)-3-[(S)-(3,5-dichlorophenoxy)phenylmethyl]pyrrolidine-1-carboxylic acid t-butyl ester (14.0 g, 33.1 mmol) was dissolved in EtOH (100 mL, 2 mol). Into the mixture was added an HCl solution prepared by the slow addition of acetyl chloride (23.6 mL, 331 mmol) into EtOH (50 mL, 860 mmol) at 0° C. The mixture was stirred at room temperature overnight. The solvent was removed by rotary evaporation, EtOAc (200 mL) was added, followed by removal of most of the solvent. EtOAc (50 mL) was added, the solution was heated to 75° C. for 15 minutes, cooled to room temperature, filtered and dried to yield (R)-3-[(S)-(3,5-dichlorophenoxy)phenylmethyl]pyrrolidine as an HCl salt (10.5 g, >99% purity).

Aufarbeitung

  1. customThe solvent was removed by rotary evaporation, EtOAc (200 mL)
  2. additionwas added
  3. customfollowed by removal of most of the solvent
  4. additionEtOAc (50 mL) was added
  5. temperaturethe solution was heated to 75° C. for 15 minutes
  6. temperaturecooled to room temperature
  7. filtrationfiltered
  8. customdried

Quellen und Nachweise

ORD-Eintrag
ord-38db1b31405844718fffd65fb27aac72
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08933249B2

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