Benzene → HCID 53846892, compound

HRID 1901176Notes

Reaction equation

HRID 1901176 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].[OH:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH2:19][C:20](=O)[CH3:21])=[CH:14][C:13]=1[CH2:23][C:24]([O:26][CH3:27])=[O:25].C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH3:27][O:26][C:24]([CH2:23][C:13]1[CH:14]=[C:15]([CH:16]=[CH:17][C:12]=1[OH:11])[O:18][CH2:19][CH:20]([NH:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4])[CH3:21])=[O:25]

Participants

6

Reactant 4

HCID 241BenzeneHCID 1000PhenylethanolamineHCID 5003444Sodium cyanoborohydrideHCID 54416855HCID 54416855, compound

Product 1

HCID 53846892HCID 53846892, compoundYield 3.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 6, but using 0.72 g of 2-amino-1-phenylethanol, 1.5 g of methyl 2-hydroxy-5-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 21), 60 ml of benzene, 50 ml of absolute methanol and 1.9 g of sodium cyanoborohydride, and then purifying the reaction product by column chromatography through silica gel, using a 10:1 by volume mixture of ethyl acetate and ethanol as the eluent, 0.07 g of the title compound was obtained having an Rf=0.40 (thin layer chromatography over silica gel, using a 10:1 by volume mixture of ethyl acetate and ethanol as the developing solvent).

Workup

  1. custompurifying the reaction product by column chromatography through silica gel
  2. additionby volume mixture of ethyl acetate and ethanol as the eluent

Sources & evidence

ORD record
ord-811ee03ceb0645c896e78cd41d857997
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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