1-二苯甲基-2-羟甲基氮杂环丁烷

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a solution of 2.36 g (17.7 mmoles) of N-chlorosuccinimide in 40 ml of dry toluene is added 1.77 ml (24.2 mmoles) of dimethyl sulfide, and the mixture is stirred at the same temperature for 25 minutes and cooled to -25° C. to -30° C. A solution of 3 g (11.8 mmoles) of 1-diphenylmethyl-2-hydroxymethylazetidine in 8 ml of toluene is dropwise added thereto in a period of 20 minutes and the mixture is stirred at the same temperature for 2 hours. A solution of 2.5 ml (11.8 mmoles) of triethylamine in 2 ml of toluene is dropwise added thereto in a period of 15 minutes. The reaction mixture is stirred at -25° C. for 30 minutes, mixed with 120 ml of ether, stirred at room temperature for 5 minutes, washed twice with 50 ml of water, dried over sodium sulfate and evaporated under reduced pressure. The resulting syrupy residue (3.2 g) is dissolved in 50 ml of methylene chloride and extracted four times with 20 (w/w) % aqueous sodium hydrogensulfite solution. The extract is washed with 20 ml of methylene chloride, adjusted to pH 10 with 20% aqueous sodium carbonate solution, and extracted four times with 50 ml of methylene chloride. The extract is washed with water, dried over sodium sulfate and evaporated under reduced pressure. The resulting syrupy residue (2.1 g) is recrystallized from a mixture of n-hexane and ether to yield 2 g of 1-diphenylmethyl-2-formylazetidine in 67% yield. cooled to -25° C. to -30° C in a period of 20 minutes the mixture is stirred at the same temperature for 2 hours in a period of 15 minutes The reaction mixture is stirred at -25° C. for 30 minutes stirred at room temperature for 5 minutes washed twice with 50 ml of water dried over sodium sulfate evaporated under reduced pressure The resulting syrupy residue (3.2 g) is dissolved in 50 ml of methylene chloride extracted four times with 20 (w/w) % aqueous sodium hydrogensulfite solution The extract is washed with 20 ml of methylene chloride extracted four times with 50 ml of methylene chloride The extract is washed with water dried over sodium sulfate evaporated under reduced pressure The resulting syrupy residue (2.1 g) is recrystallized from a mixture of n-hexane and ether

反应条件: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a suspension of 0.57 g of lithium aluminium hydride in 30 ml of dry ether is dropwise added a solution of 6 g (0.021 mole) of 1-diphenylmethyl-2-methoxycarbonylazetidine [prepared in the manner described in J. Heterocyclic Chem., 6, 435 (1969) by R. M. Rodebaugh and N. H. Cromwell] in 30 ml of dry ether in a period of 15 minutes, and the mixture is stirred at room temperature for 15 minutes. The excess amount of lithium aluminium hydride is decomposed with ethyl acetate. The insoluble materials are filtered off and washed with dry ether. The combined filtrate and washings are evaporated to dryness under reduced pressure. The residue is dissolved in ether and the resulting solution is evaporated to yield 4.7 g of crude syrupy 1-diphenylmethyl-2-hydroxymethylazetidine in 90% yield. prepared in the manner The insoluble materials are filtered off washed with dry ether The combined filtrate and washings are evaporated to dryness under reduced pressure The residue is dissolved in ether the resulting solution is evaporated