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

HRID 1079029ノート

反応式

HRID 1079029 の反応式
[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]

参加物

5

反応物 3

HCID 712FormaldehydeHCID 8021DiethylamineHCID 15086767HCID 15086767、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

A mixture of 3.0 g of (S)-3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-propargyl-2pyrrolidinone, 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)dimethylsily]oxy]-2-pyrrolidinone as a yellow oil. [α]D26 =-56 (methylene chloride).

後処理

  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)

出典と根拠

ORDレコード
ord-050e276b014346d2a01147d53e93c89d
出典データセット
uspto-grants-1996_08
特許番号
US05550257

反応ノート

読み込み中…