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

HRID 1707962Notes

Reaction equation

HRID 1707962 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 is 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)dimethylsilyl]oxy]-2-pyrrolidinone as a yellow oil. [α]D26° =-56 (methylene chloride).

Workup

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

Sources & evidence

ORD record
ord-37aadaec828c42d792da248da8dc7a6d
Source dataset
uspto-grants-1994_10
Patent number
US05356885

Reaction notes

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