Sodium hydride → HCID 86610748, compound

HRID 269978Notes

Reaction equation

HRID 269978 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N+]([O-])=O)=[C:4](F)[CH:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH:21]([OH:24])[CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].[H-].[Na+]>CN(C=O)C>[C:12]([O:16][C:17]([N:19]1[CH2:23][CH2:22][CH:21]([O:24][C:4]2[CH:3]=[C:2]([Cl:1])[CH:7]=[CH:6][C:5]=2[CH2:23][CH2:22][CH:21]=[O:24])[CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 696914-Chloro-2-fluoro-1-nitrobenzeneHCID 44169391-Boc-3-pyrrolidinol

Product 1

HCID 86610748HCID 86610748, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 4-chloro-2-fluoro-1-nitrobenzene (2 g, 11.40 mmol) and 3-hydroxypyrrolidine-1-carboxylic acid tert-butyl ester in 40 mL of anhydrous DMF, add NaH (0.55 g, 22.79 mmol) at 0° C. in portions. Stir the mixture at room temperature for 1 h, then, pour into ice-water, extract with EtOAc (3×50 mL), dry over MgSO4 and evaporate to afford the compound pure enough to use in the following step without further purification (yellow solid, 4.15 g). Follow a procedure similar to preparation 49 substituting 3-(5-chloro-2-nitro-phenoxy)-pyrrolidine-1-carboxylic acid tert butyl ester for 1-(5-chloro-2-nitro-phenyl)-pyrrolidine to prepare the title compound.

Workup

  1. extractionextract with EtOAc (3×50 mL)
  2. dry with materialdry over MgSO4
  3. customevaporate
  4. customto afford the compound pure enough
  5. customto use in the following step without further purification (yellow solid, 4.15 g)
  6. customsimilar to preparation 49 substituting 3-(5-chloro-2-nitro-phenoxy)-pyrrolidine-1-carboxylic acid tert butyl ester for 1-(5-chloro-2-nitro-phenyl)-pyrrolidine

Sources & evidence

ORD record
ord-a2369bf2f1294ce5ba4f532be926bac7
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Reaction notes

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