Benzene → HCID 53747377, compound

HRID 1901158Notes

Reaction equation

HRID 1901158 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH:8]=[CH:7][CH:6]=1)[OH:4].O=[C:16]([CH3:30])[CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([CH2:25][C:26]([O:28][CH3:29])=[O:27])=[CH:21][CH:20]=1.C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH3:29][O:28][C:26]([CH2:25][C:22]1[CH:21]=[CH:20][C:19]([O:18][CH2:17][CH:16]([NH:1][CH2:2][CH:3]([C:5]2[C:14]3[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:8]=[CH:7][CH:6]=2)[OH:4])[CH3:30])=[CH:24][CH:23]=1)=[O:27]

Participants

6

Reactant 4

HCID 241BenzeneHCID 5003444Sodium cyanoborohydrideHCID 167681362-Amino-1-(naphthalen-1-yl)ethan-1-olHCID 21832178Methyl 4-(2-oxopropoxy)phenylacetate

Product 1

HCID 53747377HCID 53747377, compoundYield 30.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 6, but using 3 g of 2-amino-1-(1-naphthyl)ethanol (prepared as described in Preparation 10), 3.87 g of methyl 4-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 3), 60 ml of benzene, 50 ml of absolute methanol and 3 g of sodium cyanoborohydride, 1.9 g of the title compound were obtained having an Rf=0.35 (thin layer chromatography over silica gel, using ethyl acetate as the developing solvent).

Sources & evidence

ORD record
ord-66baacbbf8414612a5b6d7be0b365b23
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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