3-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (S)-(-)- → HCID 68839236, compound

HRID 660559

Reaction equation

HRID 660559 reaction equation
[Br-].[CH2:2]([O:4][C:5]([C:7]1[CH:32]=[CH:31][CH:30]=[CH:29][C:8]=1[CH2:9][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)=[O:6])[CH3:3].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:43]([O:47][C:48]([N:50]1[C@H:54]([CH:55]=O)[CH2:53][O:52][C:51]1([CH3:58])[CH3:57])=[O:49])([CH3:46])([CH3:45])[CH3:44]>C1(C)C=CC=CC=1>[C:43]([O:47][C:48]([N:50]1[C@H:54]([CH:55]=[CH:9][C:8]2[CH:29]=[CH:30][CH:31]=[CH:32][C:7]=2[C:5]([O:4][CH2:2][CH3:3])=[O:6])[CH2:53][O:52][C:51]1([CH3:57])[CH3:58])=[O:49])([CH3:46])([CH3:44])[CH3:45]

Participants

5

Reactant 3

HCID 1798243-Boc-2,2-dimethyloxazolidine-4-carboxaldehyde, (S)-(-)-HCID 3251421Potassium bis(trimethylsilyl)amideHCID 19092713{[2-(Ethoxycarbonyl)phenyl]methyl}(triphenyl)phosphanium bromide

Product 1

HCID 68839236HCID 68839236, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a suspension of (2-ethoxycarbonylbenzyl)-triphenylphosphonium bromide (9.0 g, 17.77 mmol) in toluene (100 mL) is added potassium bis(trimethylsilyl)amide (0.5M in toluene, 40 mL) followed by the addition of (S)-4-formyl-2,2-dimethyloxazolidine-3-carboxylic acid tert-butyl ester (3.4 g, 14.83 mmol) and the mixture is refluxed for 1 h. After cooling to RT, ice/water is added and the solution extracted with EtOAc. The organic layer is washed with brine, dried over MgSO4, filtered and concentrated. The crude material is purified by column chromatography to afford the title compound as a yellow oil: (M+1)+=376.

Workup

  1. temperaturethe mixture is refluxed for 1 h
  2. extractionthe solution extracted with EtOAc
  3. washThe organic layer is washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude material is purified by column chromatography

Sources & evidence

ORD record
ord-4796e25e8e5a4414b94bcacc3d4b7926
Source dataset
uspto-grants-2011_12
Patent number
US08084448B2

Linked notes

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