Hydrochloric Acid → HCID 59536645, compound

HRID 1922177Notes

Reaction equation

HRID 1922177 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][C@H:10]([CH:13]([O:18][C:19]2[C:20]([CH3:28])=[N:21][C:22]([O:25][CH2:26][CH3:27])=[CH:23][CH:24]=2)[CH2:14][CH:15]([CH3:17])[CH3:16])[CH2:9]1)=O)(C)(C)C.Cl>>[CH2:26]([O:25][C:22]1[N:21]=[C:20]([CH3:28])[C:19]([O:18][CH:13]([C@H:10]2[CH2:11][CH2:12][NH:8][CH2:9]2)[CH2:14][CH:15]([CH3:16])[CH3:17])=[CH:24][CH:23]=1)[CH3:27]

Participants

3

Reactant 2

HCID 313Hydrochloric AcidHCID 66734530HCID 66734530, compound

Product 1

HCID 59536645HCID 59536645, compoundYield 21%

Procedure

Stir a mixture of (3S)-3-[1-(6-ethoxy-2-methyl-3-pyridyloxy)-3-methyl-butyl]-pyrrolidine-1-carboxylic acid tert-butyl ester (S-2) and aqueous HCl (4N in dioxane, 0.261 mL, 1.04 mmol) at room temperature for 1 hour. After full conversion, concentrate the mixture, dissolve the residue in chloromethane and load onto a pre-packed SCX column. Wash the column with dichloromethane followed by methanol. Release the product with 2M NH3 in methanol and concentrate under reduced pressure. Purify the crude residue by reverse phase chromatography (34-60% gradient actonitrile in 0.01 M ammoniumformate in water, 85 mL/min, for 8 min., C18 ODB XBridge column, 30×75 mm, 5 μm) to give 13.4 mg (21%) of (3S)-3-[1-(6-ethoxy-2-methyl-3-pyridyloxy)-3-methyl-butyl]-pyrrolidine (S-2). MS (m/z)=293 [M+1].

Workup

  1. concentrationAfter full conversion, concentrate the mixture
  2. dissolutiondissolve the residue in chloromethane
  3. washWash the column with dichloromethane
  4. concentrationconcentrate under reduced pressure
  5. customPurify the crude residue by reverse phase chromatography (34-60% gradient actonitrile in 0.01 M ammoniumformate in water, 85 mL/min, for 8 min., C18 ODB XBridge column, 30×75 mm, 5 μm)

Sources & evidence

ORD record
ord-8c1dd185049c4182926ffe9b8ee3d4e4
Source dataset
uspto-grants-2012_05
Patent number
US08173821B2

Reaction notes

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