Hydrochloric Acid → (1S,4S)-2-(2,3-dichlorobenzoyl)-2,5-diazabicyclo[2.2.1]heptane

HRID 421992Notes

Reaction equation

HRID 421992 reaction equation
[Cl:1][C:2]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([N:6]1[CH2:11][C@@H:10]2[CH2:12][C@H:7]1[CH2:8][N:9]2C(OC(C)(C)C)=O)=[O:5].CO.Cl>O1CCOCC1>[Cl:1][C:2]1[C:23]([Cl:24])=[CH:22][CH:21]=[CH:20][C:3]=1[C:4]([N:6]1[CH2:11][C@@H:10]2[CH2:12][C@H:7]1[CH2:8][NH:9]2)=[O:5]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 66676957tert-butyl (1S,4S)-5-(2,3-dichlorobenzoyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate

Product 1

HCID 66676753(1S,4S)-2-(2,3-dichlorobenzoyl)-2,5-diazabicyclo[2.2.1]heptane

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a mixture of 5.5 g of tert-butyl (1S,4S)-5-(2,3-dichlorobenzoyl)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate and 10 ml of methanol was added hydrochloride in 1,4-dioxane solution (4 mol/l, 20 ml) followed by stirring for 1.5 hour at room temperature. The reaction mixture was concentrated in vacuo and then the resulting residue was suspended with diethylether. The precipitate was filtered and dried to give a crystal of the title compound.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. filtrationThe precipitate was filtered
  3. customdried

Sources & evidence

ORD record
ord-96376c2227c14e0babc4215e50d7baf9
Source dataset
uspto-grants-2012_01
Patent number
US08101621B2

Reaction notes

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