Benzene → HCID 21832133, compound

HRID 1682714Notes

Reaction equation

HRID 1682714 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=1)[OH:4].[CH2:12]([O:14][C:15]([C:17]([C:34]1[CH:44]=[CH:43][C:37]([O:38][CH2:39][C:40](=O)[CH3:41])=[CH:36][CH:35]=1)([C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:18]([C:24]([O:26][CH2:27][CH3:28])=[O:25])[C:19]([O:21][CH2:22][CH3:23])=[O:20])=[O:16])[CH3:13].C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH2:32]([O:31][C:29]([C:17]([C:34]1[CH:44]=[CH:43][C:37]([O:38][CH2:39][CH:40]([NH:1][CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=2)[OH:4])[CH3:41])=[CH:36][CH:35]=1)([C:15]([O:14][CH2:12][CH3:13])=[O:16])[CH:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])[C:24]([O:26][CH2:27][CH3:28])=[O:25])=[O:30])[CH3:33]

Participants

6

Reactant 4

HCID 241BenzeneHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 5003444Sodium cyanoborohydrideHCID 21832142HCID 21832142, compound

Product 1

HCID 21832133HCID 21832133, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 6, but using 1 g of 2-amino-1-(3-chlorophenyl)ethanol (prepared as described in Preparation 8), 3 g of 4-[1,1,2,2-tetrakis(ethoxycarbonyl)ethyl]phenoxyacetone (prepared as described in Preparation 22), 100 ml of dry benzene, 50 ml of absolute methanol and 920 mg 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 hexane as the eluent, 0.4 g of the title compound was obtained having an Rf=0.35 (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
  2. additionby volume mixture of ethyl acetate and hexane as the eluent

Sources & evidence

ORD record
ord-b255e2fa1e0b4ad4b98dba2cf24e0ba0
Source dataset
uspto-grants-1997_06
Patent number
US05635534

Reaction notes

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