Hydrochloric Acid → HCID 59536633, compound

HRID 1922189Notes

Reaction equation

HRID 1922189 reaction equation
Cl.C(OC([N:9]1[CH2:13][CH2:12][C@H:11]([CH:14]([O:19][C:20]2[C:21]([CH3:27])=[N:22][C:23]([Cl:26])=[CH:24][CH:25]=2)[CH2:15][CH:16]2[CH2:18][CH2:17]2)[CH2:10]1)=O)(C)(C)C>ClCCl>[Cl:26][C:23]1[N:22]=[C:21]([CH3:27])[C:20]([O:19][CH:14]([C@H:11]2[CH2:12][CH2:13][NH:9][CH2:10]2)[CH2:15][CH:16]2[CH2:17][CH2:18]2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 59536659HCID 59536659, compound

Product 1

HCID 59536633HCID 59536633, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Add HCl (4M in 1,4-dioxane, 52.7 mL, 627 mmol) to a solution of (3S)-3-[1-(6-chloro-2-methyl-3-pyridyloxy)-2-cyclopropyl-ethyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (S-1) (13.4 g, 35.2 mmol) in dichloromethane (40.2 mL). Stir under nitrogen at room temperature for 1 h. Evaporate the solvent and dissolve the residue in a mixture of t-butylmethylether (40 mL) and water (40 mL). Separate the phases, wash the aqueous phase with t-butylmethylether (2×). Adjust the pH of the aqueous phase to 9 by the addition of 10% aqueous K2CO3, extract with t-butylmethylether (3×). Wash the combined organic phases with water and brine. Evaporate the volatiles to obtain (3S)-3-[1-(6-chloro-2-methyl-3-pyridyloxy)-2-cyclopropyl-ethyl]-pyrrolidine (S-1) (9.6 g, 97%). MS (m/z)=281.2 [M+1]

Workup

  1. customEvaporate the solvent
  2. dissolutiondissolve the residue
  3. additionin a mixture of t-butylmethylether (40 mL) and water (40 mL)
  4. customSeparate the phases
  5. washwash the aqueous phase with t-butylmethylether (2×)
  6. additionby the addition of 10% aqueous K2CO3
  7. extractionextract with t-butylmethylether (3×)
  8. washWash the combined organic phases with water and brine
  9. customEvaporate the volatiles

Sources & evidence

ORD record
ord-59311ebc8fb54cd1a56e5c223fb52cb5
Source dataset
uspto-grants-2012_05
Patent number
US08173821B2

Reaction notes

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