ChemicalBook CAS DataBase List 3-Aza-bicyclo[3.3.1]nonane-3,7-dicarboxylic acid 3-tert-butyl ester

3-Aza-bicyclo[3.3.1]nonane-3,7-dicarboxylic acid 3-tert-butyl ester synthesis

3synthesis methods

Product Name:3-Aza-bicyclo[3.3.1]nonane-3,7-dicarboxylic acid 3-tert-butyl ester
CAS Number:1068584-98-4
Molecular formula:C14H23NO4
Molecular Weight:269.34

3-Azabicyclo[3.3.1]nonane-3,7-dicarboxylic acid, 3-(1,1-dimethylethyl) 7-methyl ester

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3-Aza-bicyclo[3.3.1]nonane-3,7-dicarboxylic acid 3-tert-butyl ester

1068584-98-4
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Yield:1068584-98-4 100%

Reaction Conditions:

Stage #1: 3-tert-butyl 7-methyl 3-azabicyclo[3.3.1]nonane-3,7-dicarboxylatewith methanol;lithium hydroxide;water in tetrahydrofuran at 30; for 16 h;
Stage #2: with hydrogenchloride in water;

Steps:

11

3-(tert-Butoxycarbonv?- 3-azabicvclor3.3.1 lnonane-7-carboxylic acid: Methyl 3-(tert-butoxycarbonyl)-3-azabicyclo[3.3.1]nonane-7-carboxylate (1.62 g, 5.72 mmol) was dissolved in a 2:1 :2 mixture of THF / water / methanol (25 ml_), and lithium hydroxide monohydrate (0.721 g, 17.2 mmol) was added. The reaction mixture was stirred at 30°C for 16 h. The volatile solvents were removed by rotary evaporation, and the residue was acidified with 2 N hydrochloric acid and extracted with ethyl acetate (2 x 50 mL). The combined organic extracts were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to give 1.53 g (100% crude yield) of 3-(tert-butoxycarbonyl)-3- azabicyclo[3.3.1]nonane-7-carboxylic acid, as a colorless solid (¹H NMR ( CDCI₃): δ 3.95-3.8 (m, 2H), 2.85-2.75 (m, 2H), 2.60-2.47 (m, 1H), 2.20-2.12 (m, 2H), 2.0- 1.85 (m, 4H), 1.60-1.70 (m, 2H), 1.41 (s, 9H); (LC-MS (MH⁺): 270).

References:

WO2008/121686,2008,A1 Location in patent:Page/Page column 63

79099-07-3 Synthesis

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References

1-BOC-4-(1-PYRROLIDINYL)-3,6-DIHYDRO-2H-PYRIDINE

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References