Trifluoroacetic acid → (1S,6R)-8-Cbz-3,8-diazabicyclo[4.2.0]octane

HRID 2175008Notes

Reaction equation

HRID 2175008 reaction equation
[C@H:1]12[N:8]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH2:7][C@H:6]1[CH2:5][CH2:4][N:3](C(OC(C)(C)C)=O)[CH2:2]2.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C@H:1]12[N:8]([C:9]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:10])[CH2:7][C@H:6]1[CH2:5][CH2:4][NH:3][CH2:2]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67086554Cis-8-Benzyl 3-Tert-Butyl 3,8-Diazabicyclo[4.2.0]Octane-3,8-Dicarboxylate

Product 1

HCID 71432745(1S,6R)-8-Cbz-3,8-diazabicyclo[4.2.0]octane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (1S,6R)-8-benzyl 3-tert-butyl 3,8-diazabicyclo[4.2.0]octane-3,8-dicarboxylate (300 mg, 0.9 mmol) in CH2Cl2 was added TFA (1:1). After 2 h, the reaction was concentrated and used without further purification.

Workup

  1. concentrationthe reaction was concentrated
  2. customused without further purification

Sources & evidence

ORD record
ord-b619a0c550e8467fbd8ad895002839d3
Source dataset
uspto-grants-2015_06
Patent number
US09062044B2

Reaction notes

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