Triphenylphosphine → (1RS,2RS,4E)-2-(4-chlorophenyl)-1-methyl-5-(2-naphthyl)-4-pentenylamine

HRID 263678ノート

反応式

HRID 263678 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12]/[CH:13]=[CH:14]/[C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[CH:9](O)[CH3:10])=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[N:44](C(OCC)=O)=NC(OCC)=O.C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([CH2:12]/[CH:13]=[CH:14]/[C:15]2[CH:24]=[CH:23][C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=2)[CH:9]([NH2:44])[CH3:10])=[CH:4][CH:3]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 199401P,P-Diphenylphosphinic azideHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19038652(2RS,3SR,5E)-3-(4-chlorophenyl)-6-(2-naphthyl)-5-hexen-2-ol

生成物 1

HCID 19038665(1RS,2RS,4E)-2-(4-chlorophenyl)-1-methyl-5-(2-naphthyl)-4-pentenylamine

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

4.06 g of (2RS,3SR,5E)-3-(4-chlorophenyl)-6-(2-naphthyl)-5-hexen-2-ol was dissolved in 30 ml of tetrahydrofuran, and 4.77 g of triphenylphosphine, 2.89 ml of diethyl azodicarboxylate and 4.77 g of diphenylphosphoryl azide were added under cooling with ice with stirring, followed by stirring at room temperature for 30 minutes. The reaction solution was evaporated to dryness under reduced pressure. Then, the residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/1→30/1). The obtained azide product was heated and refluxed together with 3.2 g of triphenylphosphine in 100 ml of 10% water-containing tetrahydrofuran. The reaction solution was evaporated to dryness under reduced pressure. Then, the residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1→20/1) to obtain 2.30 g of the above-identified compound.

後処理

  1. temperatureunder cooling with ice
  2. stirringby stirring at room temperature for 30 minutes
  3. customThe reaction solution was evaporated to dryness under reduced pressure
  4. customThen, the residue was purified by silica gel column chromatography (hexane/ethyl acetate=50/1→30/1)
  5. temperatureThe obtained azide product was heated
  6. temperaturerefluxed together with 3.2 g of triphenylphosphine in 100 ml of 10% water-
  7. additioncontaining tetrahydrofuran
  8. customThe reaction solution was evaporated to dryness under reduced pressure
  9. customThen, the residue was purified by silica gel column chromatography (methylene chloride/methanol=50/1→20/1)

出典と根拠

ORDレコード
ord-9fd94f574bca4effbec998a65c3ee4f4
出典データセット
uspto-grants-1997_07
特許番号
US05643958

反応ノート

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