Benzene → 2-[2-(4-Methoxycarbonylmethylphenoxy)-1-methylethyl]amino-1-(3,4,5-trimethoxyphenyl)ethanol

HRID 1901163Notes

Reaction equation

HRID 1901163 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[C:9]([O:11][CH3:12])[C:8]([O:13][CH3:14])=[C:7]([O:15][CH3:16])[CH:6]=1)[OH:4].O=[C:18]([CH3:32])[CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([CH2:27][C:28]([O:30][CH3:31])=[O:29])=[CH:23][CH:22]=1.C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH3:31][O:30][C:28]([CH2:27][C:24]1[CH:23]=[CH:22][C:21]([O:20][CH2:19][CH:18]([NH:1][CH2:2][CH:3]([C:5]2[CH:6]=[C:7]([O:15][CH3:16])[C:8]([O:13][CH3:14])=[C:9]([O:11][CH3:12])[CH:10]=2)[OH:4])[CH3:32])=[CH:26][CH:25]=1)=[O:29]

Participants

6

Reactant 4

HCID 241BenzeneHCID 288942-Amino-1-(3,4,5-trimethoxyphenyl)ethanolHCID 5003444Sodium cyanoborohydrideHCID 21832178Methyl 4-(2-oxopropoxy)phenylacetate

Product 1

HCID 541202312-[2-(4-Methoxycarbonylmethylphenoxy)-1-methylethyl]amino-1-(3,4,5-trimethoxyphenyl)ethanolYield 82.3%

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-(3,4,5-trimethoxyphenyl)ethanol (prepared as described in Preparation 14), 2.35 g of methyl 4-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 3), 70 ml of benzene, 60 ml of absolute methanol and 4.8 g of sodium cyanoborohydride, 3.14 g of the title compound were obtained having an Rf=0.21 (thin layer chromatography over silica gel, using ethyl acetate as the developing solvent).

Sources & evidence

ORD record
ord-b3d9f3ed7f014b01af48f1acd58a1669
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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