Dichloromethane → (1S,4S)-5-(2-Methyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane hydrochloride

HRID 1775342Notes

Reaction equation

HRID 1775342 reaction equation
[CH3:1][C:2]1[C:7]([N:8]2[CH2:13][C@@H:12]3[CH2:14][C@H:9]2[CH2:10][N:11]3C(OC(C)(C)C)=O)=[CH:6][CH:5]=[CH:4][N:3]=1.C(Cl)[Cl:23]>FC(F)(F)C(O)=O>[ClH:23].[CH3:1][C:2]1[C:7]([N:8]2[CH2:13][C@@H:12]3[CH2:14][C@H:9]2[CH2:10][NH:11]3)=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 6344DichloromethaneHCID 131734737tert-Butyl (1S,4S)-5-(2-methyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 89825789(1S,4S)-5-(2-Methyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane hydrochlorideYield 94%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

tert-Butyl (1S,4S)-5-(2-methyl-3-pyridyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate (230 mg, 0.8 mmol) was dissolved in a mixture of DCM (5 ml) and trifluoroacetic acid (5 ml) and stirred at room temperature overnight. The mixture was concentrated under reduced pressure, the residue was dissolved in DCM and evaporated again. The last step was repeated, the residue was dissolved in THF (10 ml) and hydrochloric acid was added (4N in dioxane, 4 ml). The precipitate was isolated by centrifugation and decantation, washed with THF (2×) and dried under reduced pressure to yield 170 mg of a brown solid (0.75 mmol, yield 94%) MS (ESI) m/z=190.1 [M+1]+.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in DCM
  3. customevaporated again
  4. dissolutionthe residue was dissolved in THF (10 ml)
  5. additionhydrochloric acid was added (4N in dioxane, 4 ml)
  6. customThe precipitate was isolated by centrifugation and decantation
  7. washwashed with THF (2×)
  8. customdried under reduced pressure

Sources & evidence

ORD record
ord-8da5a53ac1c34c41a7169649f6d7ec94
Source dataset
uspto-grants-2016_02
Patent number
US09260441B2

Reaction notes

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