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CAS No. : | 81477-94-3 | MDL No. : | MFCD00134280 |
Formula : | C19H21NO2 | Boiling Point : | - |
Linear Structure Formula : | (C6H5)2CNCH2C(O)OC(CH3)3 | InChI Key : | YSHDPXQDVKNPKA-UHFFFAOYSA-N |
M.W : | 295.38 | Pubchem ID : | 688171 |
Synonyms : |
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Chemical Name : | tert-Butyl 2-((diphenylmethylene)amino)acetate |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With C37H37N2O(1+)*Br(1-); potassium hydroxide; In chloroform; water; toluene; at -40℃; for 72h; | A 10 mL reactiontube was charged with 2 (30 mg, 0.1 mmol), 3,5-dichlorobenzyl bromide (119 mg, 0.5 mmol, 5 equivalent), catalyst 1f (6 mg, 0.01 mmol, 0.1 equivalent) and toluene and CHCl3 (1.5 mL, 2:1 v/v),and the mixture was cooled to 40 C. After the mixture was stirred for 10 min, 50% aq. KOH (28L, 0.1 mmol, 5 equivalent) was added, and the whole reaction mixture was stirred at 40 C for72 h before being allowed to warm to ambient temperature. The reaction was quenched by addingH2O (2 mL), and the resulting mixture was extracted with EtOAc (3 10 mL). The combined extractswere washed with brine (10 mL) and dried (anhydrous Na2SO4), and the crude product was purifiedby flash column chromatography (eluting with hexane/EtOAc, 50:1) to afford 4a (43 mg, 95% yield)as light yellow liquid. 97% ee; []20D 178.8 (c = 1.0, CH2Cl2); 1H-NMR (400 MHz, CDCl3): 7.57 (s,1H), 7.55 (d, J = 1.4 Hz, 1H), 7.40-7.29 (m, 6H), 7.16 (t, J = 1.7 Hz, 1H), 6.95 (d, J = 1.7 Hz, 2H), 6.76(d, J = 6.1 Hz, 2H), 4.12 (dd, J = 8.9, 4.6 Hz, 1H), 3.19-3.08 (m, 2H), 1.45 (s, 9H); 13C-NMR (100 MHz,CDCl3): 171.1, 170.2, 141.7, 139.2, 136.1, 134.4, 130.3, 128.7, 128.6, 128.3, 128.3, 128.0, 127.6, 126.4, 81.6,66.9, 38.9, 28.0; HRMS (ESI, positive): Calcd. for C26H26Cl2NO2 [M + H]+ 454.1335, found: 454.1333.HPLC analysis: Daicel Chiralcel OD-H, n-hexane/isopropanol = 95:5, flow rate = 0.5 mL/min. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With C37H37N2O(1+)*Br(1-); potassium hydroxide; In chloroform; water; toluene; at -40℃; for 72h; | A 10 mL reactiontube was charged with 2 (30 mg, 0.1 mmol), 3,5-dichlorobenzyl bromide (119 mg, 0.5 mmol, 5 equivalent), catalyst 1f (6 mg, 0.01 mmol, 0.1 equivalent) and toluene and CHCl3 (1.5 mL, 2:1 v/v),and the mixture was cooled to 40 C. After the mixture was stirred for 10 min, 50% aq. KOH (28L, 0.1 mmol, 5 equivalent) was added, and the whole reaction mixture was stirred at 40 C for72 h before being allowed to warm to ambient temperature. The reaction was quenched by addingH2O (2 mL), and the resulting mixture was extracted with EtOAc (3 10 mL). The combined extractswere washed with brine (10 mL) and dried (anhydrous Na2SO4), and the crude product was purifiedby flash column chromatography (eluting with hexane/EtOAc, 50:1) to afford 4a (43 mg, 95% yield)as light yellow liquid. 97% ee; []20D 178.8 (c = 1.0, CH2Cl2); 1H-NMR (400 MHz, CDCl3): 7.57 (s,1H), 7.55 (d, J = 1.4 Hz, 1H), 7.40-7.29 (m, 6H), 7.16 (t, J = 1.7 Hz, 1H), 6.95 (d, J = 1.7 Hz, 2H), 6.76(d, J = 6.1 Hz, 2H), 4.12 (dd, J = 8.9, 4.6 Hz, 1H), 3.19-3.08 (m, 2H), 1.45 (s, 9H); 13C-NMR (100 MHz,CDCl3): 171.1, 170.2, 141.7, 139.2, 136.1, 134.4, 130.3, 128.7, 128.6, 128.3, 128.3, 128.0, 127.6, 126.4, 81.6,66.9, 38.9, 28.0; HRMS (ESI, positive): Calcd. for C26H26Cl2NO2 [M + H]+ 454.1335, found: 454.1333.HPLC analysis: Daicel Chiralcel OD-H, n-hexane/isopropanol = 95:5, flow rate = 0.5 mL/min. |