1-叔丁基-4-哌啶醇

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

实验步骤: The title compound was prepared from 40 mg of 7-bromo-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one (COMPOUND HHH2), 55 mg of 1-tert-butylpiperidin-4-ol, and 8 mg of NaH by a procedure analogous to that described in COMPOUND HHH6. Mass spectrum (ESI) 556 (M+1). 1H NMR (500 MHz, CDCl3; doubling of peaks due to restricted rotation) δ 1.44 and 1.42 (2 s, 9H); 2.20-2.53 (m, 4H); 2.77 (m, 0.6H); 3.05 (br s, 1.6H); 3.50 (m, 1.5H); 3.70 (m, 0.8H); 4.60-5.40 (m, 2.9H); 5.39 (br s, 0.8H); 5.75 and 5.80 (2 s, 1H); 6.54 and 6.56 (2 d, J=8.5 Hz and J=10 Hz, 1H); 7.36-7.66 (m, 8H).

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

实验步骤: To a 0° C. solution of 1.0 g of 1-tert-butylpiperidin-4-one (COMPOUND PPA-1) in 2 mL of THF was added 6.4 mL of a 1M solution of lithium aluminum hydride in THF dropwise. The mixture was stirred 10 min at rt, then quenched by careful addition of 0.2 mL of water, 0.2 mL of 15% aqueous NaOH, and 0.6 mL of water. The mixture was stirred vigorously for 30 min, then filtered and concentrated to yield the title compound. quenched by careful addition of 0.2 mL of water, 0.2 mL of 15% aqueous NaOH, and 0.6 mL of water The mixture was stirred vigorously for 30 min filtered concentrated

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

实验步骤: The title compound was prepared from 40 mg of 7-bromo-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one (COMPOUND HHH2), 55 mg of 1-tert-butylpiperidin-4-ol, and 8 mg of NaH by a procedure analogous to that described in COMPOUND HHH6. Mass spectrum (ESI) 556 (M+1). 1H NMR (500 MHz, CDCl3; doubling of peaks due to restricted rotation) δ 1.44 and 1.42 (2 s, 9H); 2.20-2.53 (m, 4H); 2.77 (m, 0.6H); 3.05 (br s, 1.6H); 3.50 (m, 1.5H); 3.70 (m, 0.8H); 4.60-5.40 (m, 2.9H); 5.39 (br s, 0.8H); 5.75 and 5.80 (2 s, 1H); 6.54 and 6.56 (2 d, J=8.5 Hz and J=10 Hz, 1H); 7.36-7.66 (m, 8H).

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

实验步骤: To a 0° C. solution of 1.0 g of 1-tert-butylpiperidin-4-one (COMPOUND PPA-1) in 2 mL of THF was added 6.4 mL of a 1M solution of lithium aluminum hydride in THF dropwise. The mixture was stirred 10 min at rt, then quenched by careful addition of 0.2 mL of water, 0.2 mL of 15% aqueous NaOH, and 0.6 mL of water. The mixture was stirred vigorously for 30 min, then filtered and concentrated to yield the title compound. quenched by careful addition of 0.2 mL of water, 0.2 mL of 15% aqueous NaOH, and 0.6 mL of water The mixture was stirred vigorously for 30 min filtered concentrated

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

实验步骤: The title compound was prepared from 40 mg of 7-bromo-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one (COMPOUND HHH2), 55 mg of 1-tert-butylpiperidin-4-ol, and 8 mg of NaH by a procedure analogous to that described in COMPOUND HHH6. Mass spectrum (ESI) 556 (M+1). 1H NMR (500 MHz, CDCl3; doubling of peaks due to restricted rotation) δ 1.44 and 1.42 (2 s, 9H); 2.20-2.53 (m, 4H); 2.77 (m, 0.6H); 3.05 (br s, 1.6H); 3.50 (m, 1.5H); 3.70 (m, 0.8H); 4.60-5.40 (m, 2.9H); 5.39 (br s, 0.8H); 5.75 and 5.80 (2 s, 1H); 6.54 and 6.56 (2 d, J=8.5 Hz and J=10 Hz, 1H); 7.36-7.66 (m, 8H).

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

实验步骤: To a 0° C. solution of 1.0 g of 1-tert-butylpiperidin-4-one (COMPOUND PPA-1) in 2 mL of THF was added 6.4 mL of a 1M solution of lithium aluminum hydride in THF dropwise. The mixture was stirred 10 min at rt, then quenched by careful addition of 0.2 mL of water, 0.2 mL of 15% aqueous NaOH, and 0.6 mL of water. The mixture was stirred vigorously for 30 min, then filtered and concentrated to yield the title compound. quenched by careful addition of 0.2 mL of water, 0.2 mL of 15% aqueous NaOH, and 0.6 mL of water The mixture was stirred vigorously for 30 min filtered concentrated