Sodium hydride → HCID 54458864, compound

HRID 614860Notes

Reaction equation

HRID 614860 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH2:4][O:5][CH2:6]P(OC)(OC)=O.[H-].[Na+].[CH2:16]([C@@:18]1([CH:38]=O)[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=3)[NH:28][CH:27]=2)[C:19]1=[O:37])[CH3:17]>O1CCCC1>[CH3:1][O:2][C:3](=[O:13])[C:4]([O:5][CH3:6])=[CH:38][C@:18]1([CH2:16][CH3:17])[CH2:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][C:26]2[C:34]3[C:29](=[CH:30][CH:31]=[C:32]([O:35][CH3:36])[CH:33]=3)[NH:28][CH:27]=2)[C:19]1=[O:37]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 53772516HCID 53772516, compoundHCID 54020372Methyl [(dimethoxyphosphoryl)methoxy]acetate

Product 1

HCID 54458864HCID 54458864, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

3.185 g of dimethylphosphonomethoxyacetic acid methyl ester are added dropwise at room temperature to a suspension of 360 mg of sodium hydride in 10 cc of absolute tetrahydrofuran in the absence of moisture. After stirring at room temperature for 30 minutes, a solution of 3.284 g of (S)-3-ethyl-3-formyl-N-[2-(5-methoxy-indol-3-yl)-ethyl]-2-piperidone in 10 cc of absolute tetrahydrofuran is added dropwise at room temperature to the reaction solution while stirring for 30 minutes. The reaction mixture is subsequently stirred at room temperature for a further 2 hours, poured on ice and extracted with methylene chloride. The organic phases are dried and concentrated. A yellowish oil, consisting of a mixture of the Z and E isomers of 3-{(S)-3-ethyl-1-[2-(5-methoxy-indol-3-yl)ethyl]-2-oxo-3-piperidyl}-2-methoxy-propenoic acid methyl ester, is obtained.

Workup

  1. stirringwhile stirring for 30 minutes
  2. stirringThe reaction mixture is subsequently stirred at room temperature for a further 2 hours
  3. additionpoured on ice
  4. extractionextracted with methylene chloride
  5. customThe organic phases are dried
  6. concentrationconcentrated
  7. additionA yellowish oil, consisting of a mixture of the Z and E isomers of 3-{(S)-3-ethyl-1-[2-(5-methoxy-indol-3-yl)ethyl]-2-oxo-3-piperidyl}-2-methoxy-propenoic acid methyl ester
  8. customis obtained

Sources & evidence

ORD record
ord-8028e5e021674fd1804df99e4c8a8023
Source dataset
uspto-grants-1979_03
Patent number
US04146643

Reaction notes

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