Hydrochloric Acid → (2S)-1-{[(1S,3S,4S,5S,6R)-5,6-Dihydroxy-2-azabicyclo [2.2.2]oct-3-yl]carbonyl}-2-pyrrolidinecarbonitrile Hydrochloride

HRID 456725Notes

Reaction equation

HRID 456725 reaction equation
[C:1]([C@@H:3]1[CH2:7][CH2:6][CH2:5][N:4]1[C:8]([C@@H:10]1[C@@H:15]2[CH2:16][CH2:17][C@@H:12]([C@@H:13]([OH:19])[C@H:14]2[OH:18])[N:11]1C(OC(C)(C)C)=O)=[O:9])#[N:2].[ClH:27]>C(Cl)(Cl)Cl.O1CCOCC1>[ClH:27].[OH:18][C@@H:14]1[C@H:13]([OH:19])[C@@H:12]2[CH2:17][CH2:16][C@H:15]1[C@@H:10]([C:8]([N:4]1[CH2:5][CH2:6][CH2:7][C@H:3]1[C:1]#[N:2])=[O:9])[NH:11]2

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86598887Tert-Butyl (1S,3S,4S,5S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-2-carboxylate

Product 1

HCID 11197388(2S)-1-{[(1S,3S,4S,5S,6R)-5,6-Dihydroxy-2-azabicyclo [2.2.2]oct-3-yl]carbonyl}-2-pyrrolidinecarbonitrile Hydrochloride

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl (1S,3S,4S,5S,6R)-3-{[(2S)-2-cyano-1-pyrrolidinyl]carbonyl}-5,6-dihydroxy-2-azabicyclo[2.2.2]octane-2-carboxylate obtained in Example 1-4 (122 mg) in chloroform (1 mL), was added 4N HCl in dioxane (3 mL) at room temperature. The reaction mixture was stirred for 15 minutes and the organic solvent was removed in vacuo. The residue was triturated with ethyl acetate to give the target compound as a white powder (100 mg).

Workup

  1. customthe organic solvent was removed in vacuo
  2. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-f05850de4f674457914c4a031b411786
Source dataset
uspto-grants-2007_03
Patent number
US07186731B2

Reaction notes

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