Potassium Carbonate → 1-Boc-3-(3-nitro-5-trifluoromethyl-phenoxymethyl)-azetidine

HRID 889966Notes

Reaction equation

HRID 889966 reaction equation
[C:1]([N:8]1[CH2:11][CH:10]([CH2:12][O:13]S(C)(=O)=O)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[N+:18]([C:21]1[CH:22]=[C:23](O)[CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)([O-:20])=[O:19].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.C([O-])(O)=O.[Na+].CCOC(C)=O>[C:1]([N:8]1[CH2:11][CH:10]([CH2:12][O:13][C:23]2[CH:24]=[C:25]([C:27]([F:29])([F:30])[F:28])[CH:26]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=2)[CH2:9]1)([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27562513-Hydroxy-5-nitrobenzotrifluorideHCID 21959416Tert-butyl 3-((methanesulfonyloxy)methyl)azetidine-1-carboxylate

Product 1

HCID 222494081-Boc-3-(3-nitro-5-trifluoromethyl-phenoxymethyl)-azetidine

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 1-Boc-3-methylsulfonyloxymethyl-azetidine (1.47 g), 3-nitro-5-trifluoromethyl-phenol (1.15 g) and K2CO3 (1.15 g) in DMF(20 ml) at 80° C. was stirred overnight. The reaction was cooled to RT and diluted with 25 mL of sat. NaHCO3 and 50 mL of EtOAc. The organic phase was separated and washed with brine (25 mL), dried over Na2SO4 and concentrated in vacuo. The crude compound was purified by column chromatography (50% EtOAc/hex).

Workup

  1. customThe organic phase was separated
  2. washwashed with brine (25 mL)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude compound was purified by column chromatography (50% EtOAc/hex)

Sources & evidence

ORD record
ord-53e947a2d97749ef85c954823a04b896
Source dataset
uspto-grants-2006_02
Patent number
US06995162B2

Reaction notes

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