Benzophenone imine → HCID 86671395、化合物

HRID 2403292ノート

反応式

HRID 2403292 の反応式
Cl[C:2]1[N:7]=[CH:6][C:5]([CH:8]2[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]2)=[CH:4][CH:3]=1.[C:21](=[NH:34])([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.CC(C)([O-])C.[Na+]>C1(C)C=CC=CC=1>[C:22]1([C:21](=[N:34][C:2]2[N:7]=[CH:6][C:5]([CH:8]3[O:13][CH2:12][CH2:11][N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:9]3)=[CH:4][CH:3]=2)[C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

参加物

5

反応物 3

HCID 136809Benzophenone imineHCID 23676156Sodium t-butoxideHCID 71743188HCID 71743188、化合物

生成物 1

HCID 86671395HCID 86671395、化合物収率 22%

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

反応条件

温度
100 °C

実験手順

To a stirred solution of tert-butyl (RS)-2-(6-chloropyridin-3-yl)morpholine-4-carboxylate (1.16 g) and benzophenone imine (977 μl) in toluene (35 ml) was added sodium tert-butoxide (597 mg). The reaction mixture was purged with argon for 10 min. (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (242 mg) and tris(dibenzylideneacetone)dipalladium(0) (107 mg) were added and the reaction mixture was heated at 100° C. overnight. The reaction mixture was then cooled to room temperature, poured into water and extracted twice with EtOAc. The organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by flash column chromatography (silica gel; gradient: 0% to 30% EtOAc in hexanes) to afford tert-butyl (RS)-2-(6-(diphenylmethyleneamino)pyridin-3-yl)morpholine-4-carboxylate (374 mg, 22%) as a yellow oil. MS (ISP): 444.2 ([M+H]+).

後処理

  1. customThe reaction mixture was purged with argon for 10 min. (R)-(+)-2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (242 mg) and tris(dibenzylideneacetone)dipalladium(0) (107 mg)
  2. additionwere added
  3. temperatureThe reaction mixture was then cooled to room temperature
  4. additionpoured into water
  5. extractionextracted twice with EtOAc
  6. dry with materialThe organic layers were dried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography (silica gel; gradient: 0% to 30% EtOAc in hexanes)

出典と根拠

ORDレコード
ord-bf54d4f69b494617903f0a70b0055824
出典データセット
uspto-grants-2014_08
特許番号
US08802673B2

反応ノート

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