Water → (R)-1-(2-Methoxy-4-nitrophenyl)pyrrolidin-3-ol

HRID 2040753Notes

Reaction equation

HRID 2040753 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[O:11][CH3:12].[OH:13][CH:14]1[CH2:18][CH2:17][NH:16][CH2:15]1.O>C(OCC)(=O)C.[Cl-].[Na+].O>[CH3:12][O:11][C:3]1[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=1[N:16]1[CH2:17][CH2:18][C@@H:14]([OH:13])[CH2:15]1

Participants

6

Reactant 3

HCID 962WaterHCID 705192-Chloro-5-nitroanisoleHCID 982104-Hydroxypyrrolidine

Product 1

HCID 15965522(R)-1-(2-Methoxy-4-nitrophenyl)pyrrolidin-3-olYield 82%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-chloro-5-nitroanisole (0.59 g, 3.1 mmol) and 3-hydroxy pyrrolidine (0.55 g, 6.2 mmol) was heated neat to 110° C. over night. Reaction mass was diluted with ethyl acetate and the organic layer was given water and brine wash, dried over Na2SO4, concentration yields dark red solid (0.6 g, 82% yield). LC-MS, [M+H]+=239.

Workup

  1. customReaction mass
  2. washwash
  3. dry with materialdried over Na2SO4, concentration

Sources & evidence

ORD record
ord-5b429d0e2a9445a78067798b76c7b9b2
Source dataset
uspto-grants-2013_11
Patent number
US08580959B2

Reaction notes

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