2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid benzyl ester synthesis
- Product Name:2-aza-bicyclo[3.1.0]hexane-2-carboxylic acid benzyl ester
- CAS Number:841302-36-1
- Molecular formula:C13H15NO2
- Molecular Weight:217.26
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Yield:841302-36-1 78%
Reaction Conditions:
with diethylzinc in diethyl ether at -40 - 20;
Steps:
3.3
To a solution of Step 2 olefin (4.99 g, 24.5 MMOL) in Et20 (164 mL) at 0 °C was slowly added diethylzinc (116 mL of a 1.0 M solution in hexane, 116 MMOL, 4.75 equiv), followed by ICH2CI (17.1 mL, 235 mmol, 9.58 equiv). The resulting reaction mixture was stirred at 0 °C for 6 h, kept at-40 °C overnight and then stirred at rt for 4 h. The reaction was then quenched by the addition of 25% NH4CI (65 mL) and extracted with Et20 (3 x 300 mL). The combined organic extracts were washed with 25% NH4CI (65 mL), brine (65 mL), dried (NA2SO4), filtered and concentrated under reduced pressure to give the crude product (15 g) as a yellow oil. Purification of the crude product by flash chromatography (silica gel, CH2CI2) generated the cyclopropyl product (4.17 g, 78%) as a colorless liquid : LC/MS M/Z 218 [M+H] + ; H NMR (CDCI3, 400 MHz) 6 7.26-7. 37 (m, 5H), 5.30 (s, 2H), 3.73 (t, 1H, J= 8. 8 Hz), 3.45-3. 55 (m, 1H), 3.03-3. 10 (m, 1H), 2.05-2. 15 (m, 1H), 191.-1. 97 (ddd, 1H, J = 12. 8,8. 4,2. 6 Hz), 1. 51-1. 59 (dt, 1H, J = 14.1, 5.7 Hz), 0.68-0. 76 (m, 1H), 0.53-0. 58 (m, 1H).
References:
WO2005/12249,2005,A2 Location in patent:Page/Page column 40
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