Benzene → 2-[2-(4-Methoxycarbonylmethylphenoxy)-1-methylethyl]amino-1-(3-phenoxyphenyl)ethanol

HRID 1901164Notes

Reaction equation

HRID 1901164 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=1)[OH:4].O=[C:19]([CH3:33])[CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31][CH3:32])=[O:30])=[CH:24][CH:23]=1.C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH3:32][O:31][C:29]([CH2:28][C:25]1[CH:24]=[CH:23][C:22]([O:21][CH2:20][CH:19]([NH:1][CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:6]=2)[OH:4])[CH3:33])=[CH:27][CH:26]=1)=[O:30]

Participants

6

Reactant 4

HCID 241BenzeneHCID 5003444Sodium cyanoborohydrideHCID 156336112-Amino-1-(3-phenoxyphenyl)ethan-1-olHCID 21832178Methyl 4-(2-oxopropoxy)phenylacetate

Product 1

HCID 538795212-[2-(4-Methoxycarbonylmethylphenoxy)-1-methylethyl]amino-1-(3-phenoxyphenyl)ethanolYield 33.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 6, but using 2 g of 2-amino-1-(3-phenoxyphenyl)ethanol (prepared as described in Preparation 15), 3.4 g of methyl 4-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 3), 70 ml of benzene, 60 ml of absolute methanol and 3.7 g of sodium cyanoborohydride, 1.27 g of the title compound were obtained having an Rf=0.26 (thin layer chromatography over silica gel, using ethyl acetate as the developing solvent).

Sources & evidence

ORD record
ord-916c83dbf9444fc296bc096cda9844c7
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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