Aluminium lithium hydride → 2-{2-[3,4-Bis(hydroxymethyl)phenoxy]-1-methylethyl}amino-1-(3-chlorophenyl)ethanol

HRID 1682713Notes

Reaction equation

HRID 1682713 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][C:25]=1[C:26](OC)=[O:27])[O:8][CH2:9][CH:10]([NH:12][CH2:13][CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)[OH:15])[CH3:11])=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:2][CH2:3][C:5]1[CH:6]=[C:7]([CH:23]=[CH:24][C:25]=1[CH2:26][OH:27])[O:8][CH2:9][CH:10]([NH:12][CH2:13][CH:14]([C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([Cl:22])[CH:17]=1)[OH:15])[CH3:11]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 218321612-{2-[3,4-Bis(methoxycarbonyl)phenoxy]-1-methylethyl}amino-1-(3-chlorophenyl)ethanol

Product 1

HCID 539618812-{2-[3,4-Bis(hydroxymethyl)phenoxy]-1-methylethyl}amino-1-(3-chlorophenyl)ethanolYield 47.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following a procedure similar to that described in Example 1, but using 2.53 g of 2-{2-[3,4-bis(methoxycarbonyl)phenoxy]-1-methylethyl}amino-1-(3-chlorophenyl)ethanol (prepared as described in Preparation 20), 0.91 g of lithium aluminum hydride and 100 ml of dry tetrahydrofuran, and then purifying the reaction product by column chromatography through silica gel, using a 5:1 by volume mixture of ethyl acetate and ethanol as the eluent, 1.04 g of the title compound were obtained having an Rf=0.37 (thin layer chromatography over silica gel, using a 5:1 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-0f3e9ff5fd81471a9d84cf26376459ee
Source dataset
uspto-grants-1997_06
Patent number
US05635534

Reaction notes

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