1,4-Dioxane → 1-(3-Methoxy-4-nitrophenyl)-3-pyrrolidinol

HRID 349136Notes

Reaction equation

HRID 349136 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[C:4]([O:11][CH3:12])[CH:3]=1.O1CCOCC1.[NH:19]1[CH2:23][CH2:22][C@@H:21]([OH:24])[CH2:20]1>O>[CH3:12][O:11][C:4]1[CH:3]=[C:2]([N:19]2[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20]2)[CH:7]=[CH:6][C:5]=1[N+:8]([O-:10])=[O:9]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 2759337(R)-3-PyrrolidinolHCID 27792505-Fluoro-2-nitroanisole

Product 1

HCID 219165891-(3-Methoxy-4-nitrophenyl)-3-pyrrolidinol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

8 g (46 mmol) of 4-fluoro-2-methoxy-1-nitrobenzene 1,80 ml of dioxane and 8.14 g (0.095 mol) of (R)-(+)-3-pyrrolidinol are respectively placed in the reactor. The mixture is refluxed for one hour. The reaction medium is poured into a mixture of water (100 ml)-ice (200 g). A yellow product precipitates. This product is filtered off, washed with water (3×30 ml) and then dried under vacuum at 45° C. 8.38 g (75%) of 1-(3-methoxy-4-nitrophenyl)pyrrolidin-3-ol (2) are thus recovered.

Workup

  1. temperatureThe mixture is refluxed for one hour
  2. customA yellow product precipitates
  3. filtrationThis product is filtered off
  4. washwashed with water (3×30 ml)
  5. customdried under vacuum at 45° C
  6. custom8.38 g (75%) of 1-(3-methoxy-4-nitrophenyl)pyrrolidin-3-ol (2) are thus recovered

Sources & evidence

ORD record
ord-436ebbd6ad364fab9724a6034d221130
Source dataset
uspto-grants-2007_02
Patent number
US07179301B2

Reaction notes

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