Hydrochloric Acid → Hydrochloric Acid

HRID 885617Notes

Reaction equation

HRID 885617 reaction equation
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]

Participants

6

Reactant 4

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

Product 2

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

Procedure

(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).

Workup

  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

Sources & evidence

ORD record
ord-7d50d768f96b4c5f9b8c848314c90f75
Source dataset
uspto-grants-2012_08
Patent number
US08242164B2

Reaction notes

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