Benzene → HCID 22867074, compound

HRID 1901156Notes

Reaction equation

HRID 1901156 reaction equation
[NH2:1][C@@H:2]([CH2:11][OH:12])[C@H:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:4].O=[C:14]([CH3:28])[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:19][CH:18]=1.C1C=CC=CC=1.C([BH3-])#N.[Na+]>CO>[CH3:27][O:26][C:24]([CH2:23][C:20]1[CH:19]=[CH:18][C:17]([O:16][CH2:15][CH:14]([NH:1][C@@H:2]([CH2:11][OH:12])[C@H:3]([C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=2)[OH:4])[CH3:28])=[CH:22][CH:21]=1)=[O:25]

Participants

6

Reactant 4

HCID 241BenzeneHCID 119881(S(R*,R*))-2-amino-1-phenylpropane-1,3-diolHCID 5003444Sodium cyanoborohydrideHCID 21832178Methyl 4-(2-oxopropoxy)phenylacetate

Product 1

HCID 22867074HCID 22867074, compoundYield 18.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following a procedure similar to that described in Example 6, but using 5.7 g of (1S, 2S)-(+)-2-amino-1-phenyl-1,3-propanediol, 5 g of methyl 4-(2-oxopropoxy)phenylacetate (prepared as described in Preparation 3), 250 ml of benzene, 250 ml of absolute methanol and 4.34 g of sodium cyanoborohydride, 1.54 g of the title compound were obtained having an Rf=0.27 (thin layer chromatography over silica gel, using a 2:1 by volume mixture of ethyl acetate and hexane as the developing solvent).

Sources & evidence

ORD record
ord-80afd4333d8f4275bb7386726566949b
Source dataset
uspto-grants-1996_11
Patent number
US05576340

Reaction notes

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