Hydrochloric Acid → HCID 86679112, compound

HRID 1774728Notes

Reaction equation

HRID 1774728 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[C:13](C)(C)[O:14][SiH2]C(C)(C)C)[CH:7]=1.Cl.O1CCOCC1>CO>[Br:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[CH2:13][OH:14])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178455458HCID 178455458, compound

Product 1

HCID 86679112HCID 86679112, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-bromo-5-[(S)-2-(tert-butyl-dimethyl-silanyloxymethyl)-pyrrolidin-1-yl]-pyridine (intermediate A-3 [B], 0.1 g, 0.269 mmol) in MeOH (2 mL) was added 4M HCl in dioxane (0.202 mL, 0.808 mmol) and the reaction mixture was stirred at room temperature for 1 h. The mixture was evaporated to dryness, the residue diluted with DCM, poured into aq. NaHCO3 (10 mL) and extracted with DCM (25 mL). The organic layer was dried over Na2SO4, filtered and evaporated to give the title compound (0.060 g, 87%) as a yellow oil. MS: 257.0, 259.0 (M+H+).

Workup

  1. customThe mixture was evaporated to dryness
  2. additionthe residue diluted with DCM
  3. additionpoured into aq. NaHCO3 (10 mL)
  4. extractionextracted with DCM (25 mL)
  5. dry with materialThe organic layer was dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated

Sources & evidence

ORD record
ord-6e2849b9cd344b60b705e7fdc365966e
Source dataset
uspto-grants-2016_02
Patent number
US09260408B2

Reaction notes

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