Triethylamine → HCID 14646168, compound

HRID 1638411Notes

Reaction equation

HRID 1638411 reaction equation
[CH:1]1([P:7]([CH:29]2[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]2)([C@@H:9]2[CH2:13][NH:12][C@H:11]([CH2:14][P:15]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=O)[CH2:10]2)=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C(N(CC)CC)C.Cl[SiH](Cl)Cl>C(#N)C>[CH:29]1([P:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)[C@@H:9]2[CH2:13][NH:12][C@H:11]([CH2:14][P:15]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH2:10]2)[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24811TrichlorosilaneHCID 13665150HCID 13665150, compound

Product 1

HCID 14646168HCID 14646168, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
60 °C

Procedure

In 4 ml of acetonitrile were dissolved 50 mg (0.1 m-mol) of (2S,4S)-4-dicyclohexylphosphinyl-2-diphenylphosphinylmethylpyrrolidine [X] and 42 mg (0.42 m-mol) of triethylamine, and the air in the reaction vessel was satisfactorily replaced with nitrogen. A solution of 54 mg (0.4 m-mol) of trichlorosilane in 1 ml of acetonitrile was added dropwise to the above solution under ice-cooling. After refluxing the mixture for 3 hours, the mixture was concentrated under reduced pressure at a low temperature. The residual product was dissolved in 15 ml of benzene, and 10 ml of a 30% aqueous solution of caustic soda was added to the benzene solution under ice-cooling. The mixture was stirred in nitrogen atmosphere for 30 minutes at 50°60° C. The benzene phase was separated and the aqueous phase was extracted with 10 ml of benzene. The benzene phases are combined, washed with 10 ml of water, dried over magnesium sulfate and concentrated under reduced pressure whereby 44 mg (yield: 95%) of the title compound was obtained.

Workup

  1. temperaturecooling
  2. temperatureAfter refluxing the mixture for 3 hours
  3. concentrationthe mixture was concentrated under reduced pressure at a low temperature
  4. dissolutionThe residual product was dissolved in 15 ml of benzene
  5. addition10 ml of a 30% aqueous solution of caustic soda was added to the benzene solution under ice-
  6. temperaturecooling
  7. customThe benzene phase was separated
  8. extractionthe aqueous phase was extracted with 10 ml of benzene
  9. washwashed with 10 ml of water
  10. dry with materialdried over magnesium sulfate

Sources & evidence

ORD record
ord-13f726f7dae849afae271cbd20ec09a3
Source dataset
uspto-grants-1989_11
Patent number
US04879389

Reaction notes

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