Benzene → HCID 21832155, compound

HRID 1682727Notes

Reaction equation

HRID 1682727 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=1)[OH:4].O=[C:14]([CH3:28])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=1.C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH3:27][O:26][C:24]([CH2:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH:14]([NH:1][CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH3:12])[CH:6]=2)[OH:4])[CH3:28])=[CH:22][CH:21]=1)=[O:25]

Participants

6

Reactant 4

HCID 241BenzeneHCID 5866792-Amino-1-(3-methoxyphenyl)ethanolHCID 5003444Sodium cyanoborohydrideHCID 21832178Methyl 4-(2-oxopropoxy)phenylacetate

Product 1

HCID 21832155HCID 21832155, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 3, but using 2.5 g of 2-amino-1-(3-methoxyphenyl)ethanol (prepared as described in Preparation 43), 4.0 g of methyl 4-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 3), 80 ml of benzene, 60 ml of absolute methanol and 2.75 g of sodium cyanoborohydride, and then purifying the reaction product by column chromatography through silica gel, using ethyl acetate as the eluent, 3.11 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).

Workup

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

Sources & evidence

ORD record
ord-2ee50c7dcb3d4a4c922f384fb9a68457
Source dataset
uspto-grants-1997_06
Patent number
US05635534

Reaction notes

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