Benzene → HCID 21832159, compound

HRID 1901184Notes

Reaction equation

HRID 1901184 reaction equation
N[CH2:2][CH:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=1)[OH:4].O=[C:13]([CH3:27])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][C:23]([O:25][CH3:26])=[O:24])=[CH:18][CH:17]=1.C1C=CC=CC=1.C([BH3-])#[N:35].[Na+]>CO>[CH3:26][O:25][C:23]([CH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH2:14][CH:13]([CH2:2][C:3]([NH2:35])([C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([Br:11])[CH:6]=2)[OH:4])[CH3:27])=[CH:17][CH:18]=1)=[O:24]

Participants

6

Reactant 4

HCID 241BenzeneHCID 5003444Sodium cyanoborohydrideHCID 21832178Methyl 4-(2-oxopropoxy)phenylacetateHCID 220210672-Amino-1-(3-bromophenyl)ethan-1-ol

Product 1

HCID 21832159HCID 21832159, compoundYield 56.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 3, but using 3.0 g of 2-amino-1-(3-bromophenyl)-ethanol (prepared as described in Preparation 41), 3.67 g of methyl 4-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 3), 80 ml of benzene, 60 ml of absolute methanol and 3.1 g of sodium cyanoborohydride, and then purifying the reaction product by column chromatography through silica gel, using ethyl acetate as the eluent, 3.33 g of the title compound were obtained having an Rf=0.25 (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

Sources & evidence

ORD record
ord-7daaca4ecd9e4405a5be32f62bad4e21
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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