Sodium Chloride → HCID 10130188, compound

HRID 2181151Notes

Reaction equation

HRID 2181151 reaction equation
FC(F)(F)C(O)=O.C(OC([N:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1[CH:20]=[CH:21][C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1)=O)(C)(C)C.C([O-])(O)=O.[Na+].[Na+].[Cl-]>C1(OC)C=CC=CC=1>[NH:15]1[CH2:19][CH2:18][CH2:17][C@H:16]1/[CH:20]=[CH:21]/[C:22]1[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 5234Sodium ChlorideHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 20781113HCID 20781113, compound

Product 1

HCID 10130188HCID 10130188, compoundYield 73.1%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Procedure

Under a nitrogen atmosphere, trifluoroacetic acid (1 mL) was added dropwise to a stirred ice-cold solution of (2S)-N-(tert-butoxycarbonyl)-2-(2-(3-pyridyl)vinyl)pyrrolidine (280 mg, 1.02 mmol) in anisole (2 mL). The reaction mixture was allowed to warm to room temperature, stirred for 16 h, then neutralized with saturated aqueous NaHCO3 solution, saturated with solid NaCl and extracted with chloroform (5×10 mL). The combined chloroform extracts were dried (K2CO3), filtered and concentrated on a rotary evaporator to give a viscous dark oil, which was chromatographed with chloroform:methanol (9:1, v/v) and 1% triethylamine as eluant. Selected fractions containing the product were combined and concentrated on a rotary evaporator to give 130 mg (73.1% yield) of a colorless oil.

Workup

  1. extractionextracted with chloroform (5×10 mL)
  2. dry with materialThe combined chloroform extracts were dried (K2CO3)
  3. filtrationfiltered
  4. concentrationconcentrated on a rotary evaporator
  5. customto give a viscous dark oil, which
  6. customwas chromatographed with chloroform:methanol (9:1
  7. additionSelected fractions containing the product
  8. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-cadf51b1bc864179865c5d5a32989c6e
Source dataset
uspto-grants-2005_05
Patent number
US06890935B2

Reaction notes

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