Formaldehyde → (S)-1-[4-diethylamino-2-butynyl]-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-pyrrolidinone

HRID 2399898Notes

Reaction equation

HRID 2399898 reaction equation
[CH3:1][C:2]([Si:5]([CH3:17])([CH3:16])[O:6][C@H:7]1[CH2:11][CH2:10][N:9]([CH2:12][C:13]#[CH:14])[C:8]1=[O:15])([CH3:4])[CH3:3].[CH2:18]=O.[CH2:20]([NH:22][CH2:23][CH3:24])[CH3:21]>C(O)(=O)C>[CH2:20]([N:22]([CH2:23][CH3:24])[CH2:18][C:14]#[C:13][CH2:12][N:9]1[CH2:10][CH2:11][C@H:7]([O:6][Si:5]([C:2]([CH3:1])([CH3:3])[CH3:4])([CH3:17])[CH3:16])[C:8]1=[O:15])[CH3:21]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8021DiethylamineHCID 15086767HCID 15086767, compound

Product 1

HCID 53818580(S)-1-[4-diethylamino-2-butynyl]-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-2-pyrrolidinone

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 3.0 g of (S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-propargyl-2-pyrrolidinone, 0.9 g of paraformaldehyde, 2.5 ml of diethylamine,3.5 ml of acetic acid and 0.050 g of cuprous chloride is stirred at room temperature for 15 minutes, followed by heating at reflux temperature for 30 minutes. The reaction As cooled, concentrated in vacuo, made basic (pH 10) with ammonium hydroxide and partitioned between methylene chloride and water. The layers are separated, the aqueous layer reextracted and the methylene chloride extracts are combined. The organic solution is dried and concentrated in vacuo with 100 ml of toluene as co-solvent the residue is purified by chromatography (alumina, activity grade 2.5, 1-5% methyl alcohol/methylene chloride) to give 3.0 g of (S)-1-[4-(diethylamino)-2-butynyl]-3-[[(1,1-dimethylethyl)dimethylsily]oxy]-2-pyrrolidinone as a yellow oil.

Workup

  1. temperatureby heating
  2. temperatureat reflux temperature for 30 minutes
  3. customThe reaction
  4. temperatureAs cooled
  5. concentrationconcentrated in vacuo
  6. custompartitioned between methylene chloride and water
  7. customThe layers are separated
  8. customThe organic solution is dried
  9. concentrationconcentrated in vacuo with 100 ml of toluene as co-solvent the residue
  10. customis purified by chromatography (alumina, activity grade 2.5, 1-5% methyl alcohol/methylene chloride)

Sources & evidence

ORD record
ord-a77ae7d90ef442ddb8733153e45b1dd3
Source dataset
uspto-grants-1995_09
Patent number
US05451685

Reaction notes

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