benzyl (1S,5S)-6-(6-chloro-5-methyl-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate → (1R,5S)-6-(6-chloro-5-methyl-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane

HRID 2251462Notes

Reaction equation

HRID 2251462 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:14][C@@H:13]3[C@H:9]2[CH2:10][N:11](C(OCC2C=CC=CC=2)=O)[CH2:12]3)=[CH:4][C:3]=1[CH3:25]>FC(F)(F)C(O)=O>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([N:8]2[CH2:14][C@@H:13]3[C@H:9]2[CH2:10][NH:11][CH2:12]3)=[CH:4][C:3]=1[CH3:25]

Participants

3

Reactant 1

HCID 23635534benzyl (1S,5S)-6-(6-chloro-5-methyl-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptane-3-carboxylate

Product 1

HCID 9813282(1R,5S)-6-(6-chloro-5-methyl-3-pyridinyl)-3,6-diazabicyclo[3.2.0]heptaneYield 80%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The product from Example 87A (220 mg, 0.61 mmol) in trifluoroacetic acid (6 mL) was heated at 60° C. for 2 hours, cooled to room temperature, concentrated, and purified by chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 90:10:1) to afford the title compound as an oil (100 mg, 80% yield). MS (DCI/NH3) m/z 224, 226 (M+H)+.

Workup

  1. concentrationconcentrated
  2. custompurified by chromatography on silica gel (CH2Cl2:MeOH:NH4OH, 90:10:1)

Sources & evidence

ORD record
ord-b4073b6ade4743ca88e911188d3437ea
Source dataset
uspto-grants-2008_01
Patent number
US07319106B2

Reaction notes

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