Benzene → 2-{2-[4-Bis(methoxycarbonyl)methylphenoxy]-1-methylethyl}amino-1-(3-chlorophenyl)ethanol

HRID 1901182Notes

Reaction equation

HRID 1901182 reaction equation
O=[C:2]([CH3:20])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:16]([O:18][CH3:19])=[O:17])[C:12]([O:14][CH3:15])=[O:13])=[CH:7][CH:6]=1.[NH2:21][CH2:22][CH:23]([C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=1)[OH:24].C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH3:19][O:18][C:16]([CH:11]([C:12]([O:14][CH3:15])=[O:13])[C:8]1[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH:2]([NH:21][CH2:22][CH:23]([C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([Cl:31])[CH:26]=2)[OH:24])[CH3:20])=[CH:10][CH:9]=1)=[O:17]

Participants

6

Reactant 4

HCID 241BenzeneHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 5003444Sodium cyanoborohydrideHCID 21832135Dimethyl 4-(2-oxopropoxy)phenylmalonate

Product 1

HCID 218322042-{2-[4-Bis(methoxycarbonyl)methylphenoxy]-1-methylethyl}amino-1-(3-chlorophenyl)ethanolYield 61.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 6, but using 0.42 g of dimethyl 4-(2-oxopropoxy)phenylmalonate (prepared as described in Preparation 38), 0.26 g of 2-amino-1-(3-chlorophenyl)ethanol (prepared as described in Preparation 8), 50 ml of dry benzene, 50 ml of absolute methanol and 0.9 g of sodium cyanoborohydride, and then purifying the reaction product by column chromatography through silica gel, using ethyl acetate as the eluent, 0.4 g of the title compound was obtained, having an Rf=0.28 (thin layer chromatography over silica gel, using ethyl acetate as the developing solvent).

Workup

  1. custompurifying the reaction product by column chromatography through silica gel

Sources & evidence

ORD record
ord-e3ae2e29baa044908065b474d8b6dffd
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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