Chlorotrimethylsilane → HCID 12047764, compound

HRID 1635063Notes

Reaction equation

HRID 1635063 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:22]2[CH2:27][CH:26](/[CH:28]=[CH:29]/[CH3:30])[O:25][C:24](=[O:31])[CH2:23]2)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C[Si](Cl)(C)C>>[CH3:11][O:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([N:22]2[CH2:27][CH:26]=[CH:28][C@@H:29]([CH3:30])[C@@H:23]2[C:24]([OH:25])=[O:31])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 2733832Lithium HexamethyldisilazideHCID 18675467HCID 18675467, compound

Product 1

HCID 12047764HCID 12047764, compound

Procedure

To a solution of lithium bis(trimethylsilyl)amide (2.67 mmol, 1.0 M in tetrahydrofuran) in tethydrofuran (5.0 ml) at −78° C. is added a solution of (±)-(E)-4-(4-methoxybenzenesulfonyl)-6-propenylmorpholine-2-one crude from the previous step. After 15 minutes, trimethylsilyl chloride (1.53 ml, 12.15 mmol) is added and the mixture warmed to room temperature. The solvent is removed (in vacuo) and replaced with toluene (10 ml). The resulting mixture is heated at 110° C. for 3 hours, cooled to room temperature and treated with 1N hydrochloric acid solution. After stirring for 10 minutes, the mixture is extracted with ethyl acetate and the combined extracts are dried (sodium sulfate), filtered and concentrated. The crude product is purified by silica gel chromatography (elution with 2:1 ethyl acetate-hexanes with 1% acetic acid) to provide (±)-(2R*,3R*)-1-(4-methoxy-benzenesulfonyl)-3-methyl-1,2,3,6-tetrahydropyridine-2-carboxylic acid.

Workup

  1. customThe solvent is removed (in vacuo)
  2. temperatureThe resulting mixture is heated at 110° C. for 3 hours
  3. temperaturecooled to room temperature
  4. additiontreated with 1N hydrochloric acid solution
  5. extractionthe mixture is extracted with ethyl acetate
  6. dry with materialthe combined extracts are dried (sodium sulfate)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product is purified by silica gel chromatography (elution with 2:1 ethyl acetate-hexanes with 1% acetic acid)

Sources & evidence

ORD record
ord-a28172e70a3f4f4a9b3248fbb2ae9f5c
Source dataset
uspto-grants-2003_01
Patent number
US06509337B1

Reaction notes

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