Water → HCID 58552948, compound

HRID 520492Notes

Reaction equation

HRID 520492 reaction equation
[NH4+].[Cl-].[CH3:3][C:4]1([CH3:20])[O:8][C@H:7]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=2)[CH2:6][O:5]1.O>C(O)(C)C.[Fe]>[CH3:3][C:4]1([CH3:20])[O:8][C@H:7]([CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=2)[NH2:17])[CH2:6][O:5]1

Participants

6

Reactant 3

HCID 962WaterHCID 25517Ammonium ChlorideHCID 58552880(R)-2,2-dimethyl-4-((3-nitrophenoxy)methyl)-1,3-dioxolane

Product 1

HCID 58552948HCID 58552948, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 3776IsopropanolSolvent

Procedure

A mixture of Fe powder (2.38 g, 42.5 mmol), NH4Cl (2.27 g, 42.5 mmol) and (R)-2,2-dimethyl-4-((3-nitrophenoxy)methyl)-1,3-dioxolane 104 (1.80 g, 7.09 mmol) in isopropanol (30 mL)/H2O (10 mL) was heated at reflux for 18 h. The crude material was filtered through a pad of Celite and the filtrate was concentrated under reduced pressure. The resulting aqueous layer was extracted with dichloromethane (3×15 mL). The combined organic layers were dried with Na2SO4, and concentrated under reduced pressure to afford 105 (1.25 g, 76% yield). The acetonide protecting group could be removed after coupling with the appropriate aniline by treatment with EtOH/3 N HCl (4:1) at reflux for 12 h.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 18 h
  3. filtrationThe crude material was filtered through a pad of Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. extractionThe resulting aqueous layer was extracted with dichloromethane (3×15 mL)
  6. dry with materialThe combined organic layers were dried with Na2SO4
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-afb0e4c33e024843abb65940c01901de
Source dataset
uspto-grants-2016_05
Patent number
US09326986B2

Reaction notes

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