Hydrochloric Acid → 2-((3R,5S)-5-(azidomethyl)pyrrolidin-3-yloxy)-5-cyclopropylpyrazine

HRID 1184616Notes

Reaction equation

HRID 1184616 reaction equation
[N:1]([CH2:4][C@@H:5]1[CH2:9][C@@H:8]([O:10][C:11]2[CH:16]=[N:15][C:14]([CH:17]3[CH2:19][CH2:18]3)=[CH:13][N:12]=2)[CH2:7][N:6]1C(OC(C)(C)C)=O)=[N+:2]=[N-:3].Cl>ClCCl.O1CCOCC1>[N:1]([CH2:4][C@H:5]1[NH:6][CH2:7][C@H:8]([O:10][C:11]2[CH:16]=[N:15][C:14]([CH:17]3[CH2:18][CH2:19]3)=[CH:13][N:12]=2)[CH2:9]1)=[N+:2]=[N-:3]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86680519(2S,4R)-tert-butyl 2-(azidomethyl)-4-(5-cyclopropylpyrazin-2-yloxy)-pyrrolidine-1-carboxylate

Product 1

HCID 866805342-((3R,5S)-5-(azidomethyl)pyrrolidin-3-yloxy)-5-cyclopropylpyrazine

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of the product from Example 174C (440 mg, 1.221 mmol) dissolved in dichloromethane (2 mL) was added 4 M HCl in 1,4-dioxane (4 mL). The resulting mixture was stirred at ambient temperature for 30 minutes and was then partitioned between saturated aqueous sodium bicarbonate and ethyl acetate. The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give the title compound.

Workup

  1. customwas then partitioned between saturated aqueous sodium bicarbonate and ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d788d802dee0486192eca4a9e909ddb5
Source dataset
uspto-grants-2014_03
Patent number
US08669255B2

Reaction notes

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