Fmoc-2-aminobicyclo[2.2.1]heptane-2-carboxylic acid (mixture of isomers) synthesis

3synthesis methods

Product Name:Fmoc-2-aminobicyclo[2.2.1]heptane-2-carboxylic acid (mixture of isomers)
CAS Number:188751-57-7
Molecular formula:C23H23NO4
Molecular Weight:377.43

82911-69-1 Synthesis

N-(9-Fluorenylmethoxycarbonyloxy)succinimide

82911-69-1
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20448-79-7 Synthesis

20448-79-7
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Fmoc-2-aminobicyclo[2.2.1]heptane-2-carboxylic acid (mixture of isomers)

188751-57-7
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Yield:188751-57-7 21%

Reaction Conditions:

Stage #1: 2-aminonorbornane-2-carboxylic acidwith hydrogenchloride in water; pH=10;
Stage #2: N-(9H-fluoren-2-ylmethoxycarbonyloxy)succinimide in water;acetonitrile at 20;

Steps:

A

2-(((9H-Fluoren-9-yl)methoxy)carbonylamino)bicyclo[2.2.1]heptane-2-carboxylic acid (compound 11 of example A): After the solution of compound 9 of example A was adjusted to pH= 10 with 2 N HCI, Fmoc-Osu (15.87 g, 45.0 mmol) and acetonitrile (50.0 mL) were added. The reaction mixture was stirred at room temperature overnight. Most of the solvent was removed under reduced pressure and the resulting mixture was adjusted to pH = 2 with 2 N HCI and extracted with DCM. The combined extracts were washed with brine, dried over anhydrous Na₂S0₄ and concentrated. The residue was purified by flash column chromatography on silica gel (DCM/MeOH = 50: 1) to afford compound 11 of example A (9.0 g, 21% yield over three steps) as a white solid.

References:

WO2012/119941,2012,A1 Location in patent:Page/Page column 111

497-38-1 Synthesis

497-38-1
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188751-57-7
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References

spiro[imidazolidine-5,2-norbornane]-2,4-dione

22264-49-9
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188751-57-7
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References