Benzene → HCID 21832195, compound

HRID 1901178Notes

Reaction equation

HRID 1901178 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].[OH:12][C:13]1[CH:14]=[C:15]([CH2:24][C:25]([O:27][CH3:28])=[O:26])[CH:16]=[CH:17][C:18]=1[O:19][CH2:20][C:21](=O)[CH3:22].C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH3:28][O:27][C:25]([CH2:24][C:15]1[CH:16]=[CH:17][C:18]([O:19][CH2:20][CH:21]([NH:1][CH2:2][CH:3]([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Cl:11])[CH:6]=2)[OH:4])[CH3:22])=[C:13]([OH:12])[CH:14]=1)=[O:26]

Participants

6

Reactant 4

HCID 241BenzeneHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-olHCID 5003444Sodium cyanoborohydrideHCID 21832183HCID 21832183, compound

Product 1

HCID 21832195HCID 21832195, compoundYield 57.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 6, but using 2 g of 2-amino-1-(3-chlorophenyl)ethanol (prepared as described in Preparation 8), 3.07 g of methyl 3-hydroxy-4-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 34), 70 ml of dry benzene, 60 ml of absolute methanol and 1.7 g of sodium cyanoborohydride, and then purifying the reaction product by column chromatography through silica gel, using ethyl acetate as the eluent, 2.62 g of the title compound were obtained as crystals, melting at 68° C.

Workup

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

Sources & evidence

ORD record
ord-a15a8cdb76ae4eafb67a9aee39706be7
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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