Benzene → 2-{2-[4-(3-Hydroxypropyl) phenoxy]-1-methylethyl}amino-1-(3-chlorophenyl) ethanol

HRID 1901152ノート

反応式

HRID 1901152 の反応式
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[OH:4].O=[C:13]([CH3:28])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24](OC)=[O:25])=[CH:18][CH:17]=1.C1C=CC=CC=1.[BH4-].[Na+]>CO>[OH:25][CH2:24][CH2:23][CH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH:13]([NH:1][CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=2)[OH:4])[CH3:28])=[CH:17][CH:18]=1

参加物

6

反応物 4

HCID 241BenzeneHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 4311764Sodium borohydrideHCID 21832185Methyl 3-[4-(2-oxopropoxy)phenyl]propionate

生成物 1

HCID 218321372-{2-[4-(3-Hydroxypropyl) phenoxy]-1-methylethyl}amino-1-(3-chlorophenyl) ethanol収率 53.8%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A procedure similar to that described in Example 2 was repeated, except that 4.3 g of 2-amino-1-(3-chlorophenyl)ethanol (prepared as described in Preparation 8), 3.5 g of methyl 3-[4-(2-oxopropoxy)phenyl]propionate (prepared as described in Preparation 5), 150 ml of benzene, 150 ml of absolute methanol and 6.12 g of sodium borohydride were used. A crude product was obtained, and this was purified by column chromatography through silica gel, using a 10:1 by volume mixture of ethyl acetate and ethanol as the eluent, to give 2.9 g of the title compound having an Rf=0.40 (thin layer chromatography over silica gel, using a 10:1 by volume mixture of ethyl acetate and ethanol as the developing solvent).

後処理

  1. customA crude product was obtained
  2. customthis was purified by column chromatography through silica gel
  3. additionby volume mixture of ethyl acetate and ethanol as the eluent

出典と根拠

ORDレコード
ord-13ab0e3673124d1f9179c9a260ad7540
出典データセット
uspto-grants-1996_11
特許番号
US05576340

反応ノート

読み込み中…