Dimethylformamide → HCID 67151639, compound

HRID 1805237

Reaction equation

HRID 1805237 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16](I)=[CH:15][CH:14]=2)[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:22][N:23](C=O)C>[C-]#N.[Zn+2].[C-]#N>[C:1]([O:5][C:6]([N:8]1[CH:12]([C:13]2[CH:18]=[CH:17][C:16]([C:22]#[N:23])=[CH:15][CH:14]=2)[CH2:11][O:10][C:9]1([CH3:21])[CH3:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6228DimethylformamideHCID 67151644(RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 67151639HCID 67151639, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 11186Zinc cyanide (Zn(CN)2)Catalyst

Procedure

A stirred solution of (RS)-4-(4-iodo-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (200 mg, example 1(e)), zinc cyanide (66 mg) and tetrakis(triphenyl-phosphine)palladium (57 mg) in DMF (4 ml) under an argon atmosphere in a sealed tube was heated at 160° C. for 15 minutes under microwave irradiation. The mixture was then poured onto ice-water and the mixture extracted twice with ethyl acetate. The combined organic extracts were washed with water, dried over sodium sulphate and concentrated in vacuo. The residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc) to give (RS)-4-(4-cyano-phenyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (82 mg, 55%) as a colourless viscous oil. MS (ISP): 325.4 ([M+Na]+), 303.4 ([M+H]+), 247.3 ([M+H—C4H8]+).

Workup

  1. additionThe mixture was then poured onto ice-water
  2. extractionthe mixture extracted twice with ethyl acetate
  3. washThe combined organic extracts were washed with water
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (SiO2; gradient: heptane/EtOAc)

Sources & evidence

ORD record
ord-99793e271f9046a3abb2050b00126617
Source dataset
uspto-grants-2013_01
Patent number
US08354441B2

Linked notes

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