Hydrochloric Acid → HCID 9942265, compound

HRID 2181156Notes

Reaction equation

HRID 2181156 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]#[C:14][C:15]1[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=1)=O)(C)(C)C.Cl>C(OCC)(=O)C>[N:17]1[CH:18]=[CH:19][CH:20]=[C:15]([C:14]#[C:13][C@@H:9]2[CH2:10][CH2:11][CH2:12][NH:8]2)[CH:16]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 69588948HCID 69588948, compound

Product 1

HCID 9942265HCID 9942265, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
2.5 °C

Procedure

An ice-cold stirred solution (S)-N-(tert-butoxycarbonyl)-2-(2-(3-pyridyl)ethynyl)pyrrolidine (300 mg, 1.10 mmol) in ethyl acetate (25 mL) was treated with concentrated hydrochloric acid (1 mL). The mixture was stirred for 10 min at 0-5° C., then for 3 h at room temperature. The layers were separated and the pH of the aqueous portion was brought to 12 with 1N NaOH. The aqueous phase was extracted with ethyl acetate (2×25 mL). The combined organic phases were washed with brine (5 mL), then dried (MgSO4), filtered and concentrated by rotary evaporation. The crude product was purified by column chromatography on silica gel, eluting with chloroform/methanol (90/10, v/v). Selected fractions containing the product were concentrated via rotary evaporation to give 0.120 g of a yellow oil.

Workup

  1. waitfor 3 h at room temperature
  2. customThe layers were separated
  3. extractionThe aqueous phase was extracted with ethyl acetate (2×25 mL)
  4. washThe combined organic phases were washed with brine (5 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe crude product was purified by column chromatography on silica gel
  9. washeluting with chloroform/methanol (90/10
  10. additionSelected fractions containing the product
  11. concentrationwere concentrated via rotary evaporation

Sources & evidence

ORD record
ord-5c3186c017f24a87ab40edbbdd456a42
Source dataset
uspto-grants-2005_05
Patent number
US06890935B2

Reaction notes

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