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

HRID 1901157Notes

Reaction equation

HRID 1901157 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)[OH:4].O=[C:16]([CH3:30])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:21][CH:20]=1.C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH3:29][O:28][C:26]([CH2:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH:16]([NH:1][CH2:2][CH:3]([C:5]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=2)[OH:4])[CH3:30])=[CH:24][CH:23]=1)=[O:27]

Participants

6

Reactant 4

HCID 241BenzeneHCID 27353792-Amino-1-(naphthalen-2-yl)ethan-1-olHCID 5003444Sodium cyanoborohydrideHCID 21832178Methyl 4-(2-oxopropoxy)phenylacetate

Product 1

HCID 539749282-[2-(4-Methoxycarbonylmethylphenoxy)-1-methylethyl]amino-1-(2-naphthyl)ethanolYield 51.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 6, but using 3 g of 2-amino-1-(2-naphthyl)ethanol (prepared as described in Preparation 9), 3.87 g of methyl 4-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 3), 60 ml of benzene, 50 ml of absolute methanol and 2.49 g of sodium cyanoborohydride, 3.23 g of the title compound were obtained having an Rf=0.15 (thin layer chromatography over silica gel, using ethyl acetate as the developing solvent).

Sources & evidence

ORD record
ord-12c4f4fe833f4709adb2c067033d5fb4
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

Loading…