ChemicalBook CAS DataBase List CAINDEXNAME:8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC

CAINDEXNAME:8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC synthesis

6synthesis methods

Product Name:CAINDEXNAME:8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC
CAS Number:50372-80-0
Molecular formula:C16H21NO2
Molecular Weight:259.34

1336-21-6 Synthesis

1336-21-6
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100-58-3
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50373-10-9 Synthesis

(1R)-TROP-2-ENE-2-CARBOXYLIC ACID METHYL ESTER

50373-10-9
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50-36-2
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CAINDEXNAME:8-AZABICYCLO[3.2.1]OCTANE-2-CARBOXYLIC

50372-80-0
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Yield:-

Reaction Conditions:

with hydrogenchloride in diethyl ether;

Steps:

1.A 2-beta-Carbomethoxy-3-beta-phenyltropane

EXAMPLE 1A 2-beta-Carbomethoxy-3-beta-phenyltropane A 2M ethereal solution of phenylmagnesium bromide (83 mL, 166 mmol) in a 500-mL 3-neck round-bottom flask equipped with mechanical stirrer, addition funnel, and nitrogen inlet tube was diluted with 83 mL of anhydrous diethyl ether and cooled to -20° C. under an atmosphere of dry nitrogen. A solution of anhydroecgonine methyl ester, prepared from cocaine (1) (15 g, 82.8 mmol) in anhydrous ether (75 mL) was added dropwise. The heterogeneous mixture was stirred for 1 h at -20° C., then poured into an equal volume of ice and water, and acidified by the dropwise addition of 2M HCl. The aqueous layer was made basic by the addition of concentrated ammonium hydroxide, saturated with NaCl, and extracted with diethyl ether. The combined extracts were dried (Na₂ SO₄) and concentrated in vacuo to give a brown oil. Bulb to bulb distillation (70° C., 0.9 Torr) of the crude product gave a pale yellow oil (16 g, 70 %). TLC analysis of the oil (silica, pentane/diethyl ether/2-propylamine, 15:5:0.8) showed it to be a mixture of the C-2 alpha and beta epimers. The beta isomer was isolated by silica gel chromatography (pentane: diethyl ether: isopropyl amine, 70:30:3). m.p. 63°-66° C. (lit: 62-64,5° C.: Clarke et al. J. Med. Chem.. 16:1260 (1973)).

References:

US5310912,1994,A

100-58-3
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$18.00/10ml

50373-10-9 Synthesis

50373-10-9
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50372-80-0
17 suppliers
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References

100-58-3
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8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 8-methyl-, methyl ester, (1R,2S,5R)-

53757-87-2
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50372-80-0
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References

ECGONINE HYDROCHLORIDE AMINO ALCOHOL POR TION

481-37-8
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50372-80-0
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References

50-36-2
2 suppliers
$15.00/1mg

50372-80-0
17 suppliers
$145.00/25mg

References