Potassium Carbonate → 3-(R)-(+)-(1-cyano-1,1-diphenylmethyl)-1-(4-hydroxymethylphenethyl)piperidine

HRID 1584164ノート

反応式

HRID 1584164 の反応式
[C:1]([C:3]([C@H:16]1[CH2:21][CH2:20][CH2:19][NH:18][CH2:17]1)([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:2].[OH:22][CH2:23][C:24]1[CH:32]=[CH:31][C:27]([CH2:28][CH2:29]Br)=[CH:26][CH:25]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:3]([C@H:16]1[CH2:21][CH2:20][CH2:19][N:18]([CH2:29][CH2:28][C:27]2[CH:31]=[CH:32][C:24]([CH2:23][OH:22])=[CH:25][CH:26]=2)[CH2:17]1)([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)#[N:2]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 22337010[4-(2-Bromoethyl)phenyl]methanolHCID 228537583-(R)-(1-cyano-1,1-diphenylmethyl)-piperidine

生成物 1

HCID 228537543-(R)-(+)-(1-cyano-1,1-diphenylmethyl)-1-(4-hydroxymethylphenethyl)piperidine

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

A mixture containing 3(R)-(+)-(1-cyano-1,1,-diphenylmethyl)-piperidine (0.28 g), 4- hydroxymethylphenethyl bromide (0.22 g), anhydrous potassium carbonate (0.28 g) and acetonitrile (10 ml) was heated under reflux for 5 hours. The mixture was partitioned between dichloromethane (30 ml) and 10% aqueous potassium carbonate (20 ml), the layers separated, and the aqueous layer extracted with dichloromethane (2×20 ml). The combined dichloromethane extracts were dried (MgSO4) and concentrated in vacuo to give an oil which was purified by column chromatography on silica eluting with hexane containing dichloromethane (30% up to 70%) then dichloromethane containing methanol (0% up to 5%). The product-containing fractions were combined and concentrated in vacuo to give an oil which was crystallised from acetonitrile to give the title compound as colourless rhombs, yield 0.21 g, m.p. 110-114° C., [α]D25 -16.2° (c, 1.0, CH2Cl2).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux for 5 hours
  3. customThe mixture was partitioned between dichloromethane (30 ml) and 10% aqueous potassium carbonate (20 ml)
  4. customthe layers separated
  5. extractionthe aqueous layer extracted with dichloromethane (2×20 ml)
  6. dry with materialThe combined dichloromethane extracts were dried (MgSO4)
  7. concentrationconcentrated in vacuo
  8. customto give an oil which
  9. customwas purified by column chromatography on silica eluting with hexane
  10. additioncontaining dichloromethane (30% up to 70%)
  11. additiondichloromethane containing methanol (0% up to 5%)
  12. concentrationconcentrated in vacuo
  13. customto give an oil which
  14. customwas crystallised from acetonitrile

出典と根拠

ORDレコード
ord-8849366b759b4372abbd2b0602781019
出典データセット
uspto-grants-1999_08
特許番号
US05932594

反応ノート

読み込み中…