ChemicalBook CAS DataBase List (1R,5S,6r)-3-tert-butyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate

(1R,5S,6r)-3-tert-butyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate synthesis

4synthesis methods

Product Name:(1R,5S,6r)-3-tert-butyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate
CAS Number:134575-37-4
Molecular formula:C13H21NO4
Molecular Weight:255.31

Ethyl 3-azabicyclo[3.1.0]hexane-6-carboxylate

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24424-99-5 Synthesis

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(1R,5S,6r)-3-tert-butyl 6-ethyl 3-azabicyclo[3.1.0]hexane-3,6-dicarboxylate

134575-37-4
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Yield:134575-37-4 82%

Reaction Conditions:

Stage #1: [(1α,5α,6α)-3-aza-bicyclo[3.1.0]hexane]-6-carboxylic acid ethyl esterwith triethylamine in dichloromethane at 0; for 0.333333 h;
Stage #2: di-tert-butyl dicarbonate in dichloromethane at 0 - 25; for 18 h;

Steps:

Ethyl (1 R,5S,6r)-3-azabicyclo[3.1 0]hexane-6-carboxylate (Intermediate 9) (2.0 g, 8.16 mmol) was dissolved in DCM (25 ml.) and triethylamine (3.45 ml_, 24.5 mmol) was added. The mixture was cooled to 0 °C, stirred for 20 mins and di-ferf-butyl dicarbonate (2.65 g, 12.2 mmol) was added. The resulting reaction mixture was then stirred at 25 °C for 18 h. The solvents were removed in-vacuo and the residue was partitioned between H₂0 (80 ml_) and ethyl acetate (60 mL). The aqueous layer was further extracted with ethyl acetate (2 ^c 60 mL), the combined organic layers were dried (Na₂S0₄) and the solvent was removed in- vacuo. The residue was purified by column chromatography (Normal- Phase activated Al₂0₃, 0 % to 40 % ethyl acetate in hexanes) to give 3-(fe/f-butyl) 6-ethyl (1 R,5S,6r)- 3-azabicyclo[3.1 .0]hexane-3,6-dicarboxylate (1.70 g, 82 %) as a liquid. LCMS (System 3, Method F): m/z 241 (M-15+H)⁺ (ESI +ve), at 4.06 min, 202 nm.

References:

WO2019/243850,2019,A1 Location in patent:Page/Page column 61