Hydrochloric Acid → HCID 69585166, compound

HRID 1795195Notes

Reaction equation

HRID 1795195 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@@H:10]([O:13][C:14]2[CH:19]=[C:18]([NH:20]C(OC(C)(C)C)=O)[CH:17]=[CH:16][C:15]=2[Cl:28])[CH2:9]1)=O)(C)(C)C.Cl>O1CCOCC1>[NH2:20][C:18]1[CH:17]=[CH:16][C:15]([Cl:28])=[C:14]([CH:19]=1)[O:13][C@@H:10]1[CH2:11][CH2:12][NH:8][CH2:9]1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21023906HCID 21023906, compound

Product 1

HCID 69585166HCID 69585166, compoundYield 77.7%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To solution of (R)-3-(5-tert-butoxycarbonylamino-2-chlorophenoxy)-pyrrolidine-1-carboxylic acid-tert-butyl ester (2 g, 4.9 mmol) in dioxane (30 mL) was added 6 N hydrogen chloride (20 mL). The reaction mixture was stirred for 2 hours, at which time it was concentrated. The resultant residue was triturated with ethyl acetate and dichloromethane, the diluted with 2.5 M potassium hydroxide (50 mL) and extracted with dichloromethane (3×50 mL). The combined organics were washed with brine (50 mL), dried over magnesium sulfate, and concentrated to give (R)-3-(5-amino-2-chlorophenoxy)-pyrrolidine (810 mg, 75%).

Workup

  1. concentrationwas concentrated
  2. customThe resultant residue was triturated with ethyl acetate and dichloromethane
  3. additionthe diluted with 2.5 M potassium hydroxide (50 mL)
  4. extractionextracted with dichloromethane (3×50 mL)
  5. washThe combined organics were washed with brine (50 mL)
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a61b793620f14e84b2c1e8eae40b3b8b
Source dataset
uspto-grants-2006_04
Patent number
US07026349B2

Reaction notes

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