Benzene → HCID 54232569, compound

HRID 1901181Notes

Reaction equation

HRID 1901181 reaction equation
[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15](=O)[CH3:16])=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[NH2:18][CH2:19][CH:20]([C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=1)[OH:21].C1C=CC=CC=1.C([BH3-])#N.[Na+]>C(O)(C)C>[C:1]([O:4][CH2:5][CH2:6][C:7]1[CH:8]=[CH:9][C:10]([O:13][CH2:14][CH:15]([NH:18][CH2:19][CH:20]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=2)[OH:21])[CH3:16])=[CH:11][CH:12]=1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 241BenzeneHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 5003444Sodium cyanoborohydrideHCID 21832202HCID 21832202, compound

Product 1

HCID 54232569HCID 54232569, compoundYield 14.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

Following a procedure similar to that described in Example 6, but using 2 g of 2-[4-(2-oxopropoxy)phenyl]ethyl acetate (prepared as described in Preparation 37), 1.45 g of 2-amino-1-(3-chlorophenyl)ethanol (prepared as described in Preparation 8), 60 ml of dry benzene, 50 ml of absolute isopropanol and 2.06 g of sodium cyanoborohydride, and then purifying the reaction product by column chromatography through silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane as the eluent, 0.49 g of the title compound was obtained, having an Rf=0.34 (thin layer chromatography over silica gel, using a 1:1 by volume mixture of ethyl acetate and hexane 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-64241da7bf154c4cb297bef11323d8eb
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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