(1-(2-Fluoro-4-nitrophenyl)pyrrolidin-2-yl)methanol → 1-(2-Fluoro-4-nitro-phenyl)-pyrrolidine-2-carbaldehyde

HRID 2236510Notes

Reaction equation

HRID 2236510 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH2:16][OH:17].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.I([O-])(=O)(=O)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-:10])=[O:9])[CH:5]=[CH:4][C:3]=1[N:11]1[CH2:15][CH2:14][CH2:13][CH:12]1[CH:16]=[O:17]

Participants

4

Reactant 2

HCID 18416155(1-(2-Fluoro-4-nitrophenyl)pyrrolidin-2-yl)methanolHCID 131723735Dess-Martin Periodate

Product 1

HCID 593003601-(2-Fluoro-4-nitro-phenyl)-pyrrolidine-2-carbaldehyde

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

[1-(2-Fluoro-4-nitro-phenyl)-pyrrolidin-2-yl]-methanol (100 mg, 0.42 mmol) and Dess-Martin periodate (175 mg, 0.42 mmol) is stirred in CH2Cl2 overnight. After chromatography, the desired product is isolated (100 mg, ˜100%): 1H NMR (300 MHz, CDCl3) 9.67 (1H, s), 7.85-7.98 (2H, m), 6.66 (1H, t, J=9.0 Hz), 4.65-4.72 (1H, m), 3.49-3.75 (2H, m), 1.89-2.30 (4H, m).

Sources & evidence

ORD record
ord-0eaa6f865b714d319dd3fe90b4e96bb4
Source dataset
uspto-grants-2010_05
Patent number
US07713994B2

Reaction notes

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