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

HRID 1901152노트

반응식

HRID 1901152 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-13ab0e3673124d1f9179c9a260ad7540
출처 데이터셋
uspto-grants-1996_11
특허 번호
US05576340

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