Formaldehyde → HCID 58911269, compound

HRID 2358233Notes

Reaction equation

HRID 2358233 reaction equation
[N:1]([C:4]1[C:5]([F:17])=[C:6]([CH:11]2[CH2:15][NH:14][C:13](=[O:16])[CH2:12]2)[CH:7]=[CH:8][C:9]=1[F:10])=[N+:2]=[N-:3].[CH2:18]=[O:19].[OH-].[Na+]>CCO>[N:1]([C:4]1[C:5]([F:17])=[C:6]([CH:11]2[CH2:15][N:14]([CH2:18][OH:19])[C:13](=[O:16])[CH2:12]2)[CH:7]=[CH:8][C:9]=1[F:10])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 58911268HCID 58911268, compound

Product 1

HCID 58911269HCID 58911269, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 50 ml three necked flask fitted with a magnetic stirrer, under inert atmosphere, a solution of 4-(3-azido-2,4-difluoro-phenyl)-pyrrolidin-2-one a14 (1.84 g, 7.73 mmol), formaldehyde (35% w/w in water, 2.3 g) and NaOH (0.015 g) in EtOH (20 ml) is heated at 60° C. for 3 h. The reaction mixture is evaporated and dried azeotropically with toluene to give the crude alcohol which is purified by chromatography on silicagel (CH2Cl2/MeOH: 98/02 (v/v)) to give 4-(3-azido-2,4-difluoro-phenyl)-1-hydroxymethyl-pyrrolidin-2-one a15 (1.64 g, 79%).

Workup

  1. customThe reaction mixture is evaporated
  2. dry with materialdried azeotropically with toluene
  3. customto give the crude alcohol which
  4. customis purified by chromatography on silicagel (CH2Cl2/MeOH: 98/02 (v/v))

Sources & evidence

ORD record
ord-07ac4a4ba2634f48b6d3719835d32622
Source dataset
uspto-grants-2010_07
Patent number
US07763644B2

Reaction notes

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