Dibenzylamine → alpha-[[Bis(phenylmethyl)amino]methyl]-3-(methoxymethyl)-4-(phenylmethoxy)benzenemethanol

HRID 1165276ノート

反応式

HRID 1165276 の反応式
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[C:7]([CH2:19][O:20][CH3:21])[CH:6]=1)=[O:4].[CH2:22]([NH:29][CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C1COCC1>[C:23]1([CH2:22][N:29]([CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][C:8]([O:11][CH2:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[C:7]([CH2:19][O:20][CH3:21])[CH:6]=2)[OH:4])[CH2:30][C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

参加物

4

反応物 2

HCID 7656DibenzylamineHCID 124989662-Bromo-1-[3-(methoxymethyl)-4-(phenylmethoxy)phenyl]ethanone

生成物 1

HCID 19862717alpha-[[Bis(phenylmethyl)amino]methyl]-3-(methoxymethyl)-4-(phenylmethoxy)benzenemethanol収率 85.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 2-bromo-1-[3-(methoxymethyl)-4-(phenylmethoxy)phenyl]ethanone (2.0 g), dibenzylamine (1.2 g) and DEA (0.8 g) in THF (30 ml) was allowed to stand at room temperature for 18 h, filtered and evaporated. The residual oil was dissolved in ethanol (20 ml) and treated portionwise with sodium borohydride (0.23 g), under nitrogen. The mixture was stirred at room temperature for 1 h, treated with methanol (20 ml), and evaporated. The residue was purified by FCC eluting with CX-ER (3:1) to give the title compound as an off-white solid (2.3 g), m.p. 52°-57°, t.l.c. (CX-ER 1:1) Rf 0.5

後処理

  1. filtrationfiltered
  2. customevaporated
  3. dissolutionThe residual oil was dissolved in ethanol (20 ml)
  4. additiontreated portionwise with sodium borohydride (0.23 g), under nitrogen
  5. additiontreated with methanol (20 ml)
  6. customevaporated
  7. customThe residue was purified by FCC
  8. washeluting with CX-ER (3:1)

出典と根拠

ORDレコード
ord-d6936fe54de6497bac92ee75bf19e192
出典データセット
uspto-grants-1990_03
特許番号
US04908386

反応ノート

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