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(2R,5S)-2-Trichloromethyl-3-oxa-1-azabicyclo[3.3.0]octan-4-one
(CAS RN:97538-67-5 Product Number:T2902)

Structure

(2R,5S)-2-Trichloromethyl-3-oxa-1-azabicyclo[3.3.0]octan-4-one

General Information

Product Number T2902

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Purity/Analysis Method >98.0%(GC)
Storage Temperature
M.F. / M.W. C7H8Cl3NO2=244.50
CAS RN 97538-67-5
Related CAS RN
MDL Number MFCD08274464
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Specification

Purity(GC) min. 98.0 %
Melting point 109.0 to 113.0 deg-C
Specific rotation [a]20/D +30.0 to +34.0 deg(C=2, Toluene)

References

Reaxys-RN 4421203
PubChem SID 253660382

Transport Information

HS Number 2934999090

Application

An Air- and Moisture-Stable Synthetic Reagent for Optically Active α-Branched Proline Derivatives

Typical procedure: Introduction of an allyl group
To a flamedried 500-mL round-bottomed flask, diisopropylamine (10 mL, 71 mmol) is added to THF (140 mL) under argon. The reaction vessel is cooled to -78 °C before n-BuLi in hexane (1.6 M, 46 mL, 74 mmol) is added. The reaction mixture is stirred for an additional 30 min at -78 °C. In a separate 250-mL round-bottomed flask, T2902 (12.2 g, 49.9 mmol) is dissolved in THF (100 mL) and cooled to 0 °C with stirring for 10 min. A cannula is used to deliver the ethereal solution to the LDA solution at -78 °C under argon over 5 min. The resulting solution is stirred for an additional 20 min before the addition of allyl bromide (7.8 mL, 90 mmol). The reaction mixture is slowly allowed to warm to -40 °C, where it is maintained for an additional 2-3 h. The reaction mixture is then poured into a 1-L separatory funnel filled with 300 mL of water. The aqueous solution is extracted with chloroform (3x300 mL). The combined organic extracts are dried over Na2SO4 and concentrated in vacuo to afford the allyl lactone (10.7 g, 75%) as an orange oil.

References

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