Triethylamine → 157824-29-8

HRID 1489517Notes

Reaction equation

HRID 1489517 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[Cl:18])[C@@H:14]([C:19]([OH:21])=O)[CH2:13][CH2:12]2.[N:22]1([CH2:27][C@@H:28]2[CH2:33][S:32][CH2:31][CH2:30][NH:29]2)[CH2:26][CH2:25][CH2:24][CH2:23]1.C(P(=O)(OCC)OCC)#N>O1CCCC1>[N:22]1([CH2:27][C@@H:28]2[CH2:33][S:32][CH2:31][CH2:30][N:29]2[C:19]([C@@H:14]2[C:15]3[C:11](=[CH:10][C:9]([Cl:8])=[C:17]([Cl:18])[CH:16]=3)[CH2:12][CH2:13]2)=[O:21])[CH2:23][CH2:24][CH2:25][CH2:26]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 76257Diethyl cyanophosphonateHCID 18645474HCID 18645474, compoundHCID 54530425HCID 54530425, compound

Product 1

HCID 133036157824-29-8Yield 56.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

9.0 ml of triethylamine were added dropwise to a solution of 14.7 g of (S)-5,6-dichloroindanecarboxylic acid in 200 ml of tetrahydrofuran at -25° to -20° C. under a stream of nitrogen and then a solution of 10.9 g of (R)-3-(1-pyrrolidinylmethyl)thiomorpholine in 50 ml of tetrahydrofuran was added dropwise thereto at the same temperature. After the solution was stirred for 10 minutes, a solution of 10.5 g of diethyl cyanophosphonate in 50 ml of tetrahydrofuran was added dropwise to the above solution and stirred at the same temperature for 30 minutes and then at 0° to 5° C. for an hour. After the tetrahydrofuran was distilled off, an aqueous solution of sodium hydrogencarbonate was added to the residue and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate. After the organic solvent was distilled off, the residue was recrystallized from a mixture of ethyl acetate and hexane to give 13.1 g of the title compound. m.p.: 123°-124° C.

Workup

  1. stirringstirred at the same temperature for 30 minutes
  2. waitat 0° to 5° C. for an hour
  3. distillationAfter the tetrahydrofuran was distilled off
  4. additionan aqueous solution of sodium hydrogencarbonate was added to the residue
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationAfter the organic solvent was distilled off
  9. customthe residue was recrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-9865dcded68d40b7a6b29810a02fdf86
Source dataset
uspto-grants-1997_10
Patent number
US05679674

Reaction notes

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