Trifluoroacetic acid → (1R,6S)-8-((1R)-1-Phenyl-ethyl)-3,8-diaza-bicyclo[4.2.0]octane

HRID 253171Notes

Reaction equation

HRID 253171 reaction equation
C(OC([N:8]1[CH2:15][CH2:14][CH:13]2[CH:10]([N:11]([C@@H:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH3:17])[CH2:12]2)[CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl>[C:18]1([C@H:16]([N:11]2[C@@H:10]3[C@@H:13]([CH2:14][CH2:15][NH:8][CH2:9]3)[CH2:12]2)[CH3:17])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 668467878-((1R)-1-Phenyl-ethyl)-3,8-diaza-bicyclo[4.2.0]octane-3-carboxylic Acid Tert-Butyl Ester

Product 1

HCID 66846137(1R,6S)-8-((1R)-1-Phenyl-ethyl)-3,8-diaza-bicyclo[4.2.0]octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the minor isomer product of Example 3E (9.3 g, 29.4 mmol) in 40 mL CH2Cl2 at 0° C. was added 20 mL trifluoroacetic acid. The ice bath was removed after the addition and the mixture stirred at ambient temperature for 3 h then was concentrated under reduced pressure and the residue was purified via column chromatography (SiO2, 1% NH4OH:9% CH3OH:90% CH2Cl2) to give the title compound. MS (DCl/NH3) m/z 217 (M+H)+.

Workup

  1. customThe ice bath was removed
  2. additionafter the addition
  3. concentrationthen was concentrated under reduced pressure
  4. customthe residue was purified via column chromatography (SiO2, 1% NH4OH:9% CH3OH:90% CH2Cl2)

Sources & evidence

ORD record
ord-8d65d7fc8cae4b0ab82c7395b9ce9e68
Source dataset
uspto-grants-2011_01
Patent number
US07872010B2

Reaction notes

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