4-(4-羟基丁基)哌啶-1-甲酸叔丁酯

反应条件: temp:0.00; pressure:0.00; stir:

反应条件: temp:0.00; pressure:0.00; stir:

实验步骤: 投料: 取50ml干燥双口瓶，加入sm1（0.1g 1eq）和乙腈，室温下加入三苯基膦（0.16g 1.4eq），氮气置换后，滴加用乙腈溶解的四溴化碳（0.17g 1.2eq ），室温下搅拌反应过夜 gcms监测，吴目标产物，tlc监测，全为原料

实验步骤: 投料: 取250ml干燥三口瓶，加入M-C4X-125463-SM1（0.1g 1eq）和超干四氢呋喃（10ml），室温搅拌下分别加入M-C4X-125463-SM2（0.25g 2eq），和三苯基膦（0.13g 1.2eq），反应液在氮气置换3次后，冰水浴下搅拌5min，逐滴加入DIAD（0.12g 1.5eq），滴加完毕后，保温搅拌30min后，升至室温下搅拌过夜。 lcms监测，结果显示，有产物ms生成。TLC监测原料反应情况（PE:EA=5:1，茚三酮显色）,左到右依次为SM1、SM2、体系、SM1上溴及混合点。最上一点为产物点，原料未反应完全，直接后处理判定结果。 后处理，反应液减压浓缩得到黄色油状物。 纯化：粗品经PLC分离纯化（PE:EA=5:1），得到无色油状物，经HNMR检测（125463-s1-p1），结构正确

实验步骤: 投料: 取250ml干燥三口瓶，加入M-C4X-125463-SM1（4.8g 18.7mmol 1eq）和超干四氢呋喃（50ml），室温搅拌下分别加入M-C4X-125463-SM2（9.5g 37.4mmol 2eq），和三苯基膦（5.88g 22.4mmol 1.2eq），反应液在氮气置换3次后，冰水浴下搅拌5min，逐滴加入DIAD（5.7ml 1.5eq 28.1mmol 1.55eq），滴加完毕后，保温搅拌30min后，升至室温下搅拌过夜。 lcms监测，结果显示，有产物ms生成。TLC监测原料反应情况（PE:EA=5:1，茚三酮显色）,左到右依次为SM1、SM2、体系及混合点。最上一点为产物点，原料反应完全。 后处理，反应液减压浓缩得到黄色油状物。 纯化：粗品经硅胶柱层析法分离纯化（PE:EA=15:1），得到淡黄色油状物9g

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

实验步骤: A mixture of 4-2 (3.4 g, 13.2 mmol), Ph3P (5.2 g, 19.8 mmol), imidazole (2.7 g, 39.6 mmol), and THF (30 mL) at ambient temperature was treated with iodine (5.0 g, 19.8 mmol) in three portions. After 1 h most of the THF was evaporated and the residue partitioned between EtOAc and H2O. The EtOAc layer was washed with H2O, 10% Na2S2O3, and brine, dried (MgSO4) and concentrated to give a solid. Flash chromatography (silica, 10% EtOAc/hexanes) gave 4-3 (3.0 g) as a light yellow oil. Rf 0.27 (silica, 10% EtOAc/hexanes). After 1 h most of the THF was evaporated the residue partitioned between EtOAc and H2O The EtOAc layer was washed with H2O, 10% Na2S2O3, and brine dried (MgSO4) concentrated to give a solid

反应条件: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 136 g (<528 mmol) 4-[1-tert-butoxycarbonylpiperidin-4-yl)-butan-1-ol (crude product), 135.3 g (516 mmol) Triphenylphosphine and 75.9 g (516 mmol) phthalimide are suspended in 1800 ml THF and 89.9 g (516 mmol) azodicarboxylic acid diethyl ester are added dropwise within three hours under protective atmosphere and light cooling (to ca. 15° C.). The mixture is left to stand at RT overnight without further cooling. Subsequently, the solvent is removed under vacuum and the oily residue is dissolved in 500 ml acetic acid ethyl ester and held at 0° C. overnight. The sedimented precipitate is filtered and discarded. The solution is concentrated under vacuum and the oily residue is chromatographically purified over silica gel with CHCl3 and crystallized from 200 ml isopropanol after drawing off the solvent. Colorless crystals remain with a MP of 100–102° C.; yield: 108.5 g (57%). The mixture is left Subsequently, the solvent is removed under vacuum the oily residue is dissolved in 500 ml acetic acid ethyl ester held at 0° C. overnight The sedimented precipitate is filtered The solution is concentrated under vacuum the oily residue is chromatographically purified over silica gel with CHCl3 crystallized from 200 ml isopropanol

反应条件: temp:15.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: 136.0 g (<528 mmol) 4-(1-tert-butoxycarbonylpiperidin-4-yl)-butan-1-ol (crude product), 135.3 g (516 mmol) triphenylphosphine and 75.9 g (516 mmol) phthalimide are suspended in THF and 89.9 g (516 mmol) azodicarboxylic acid diethyl ester are added dropwise within 3 hours under protective atmosphere and light cooling (ca. 15° C.). The mixture is left to stand at RT overnight without further cooling. Subsequently, the solvent is removed under vacuum and the oily residue is dissolved in 500 ml acetic acid ethyl ester and held overnight at 0° C. The sedimented precipitate is filtered and discarded. The solution is concentrated under vacuum and the oily residue is chromatographically purified over silica gel with CHCl3 and crystallized from 200 ml isopropanol after drawing off the solvent. Colorless crystals with a MP of 100-102° C. were recovered; yield: 108.5g (57%). The mixture is left Subsequently, the solvent is removed under vacuum the oily residue is dissolved in 500 ml acetic acid ethyl ester held overnight at 0° C The sedimented precipitate is filtered The solution is concentrated under vacuum the oily residue is chromatographically purified over silica gel with CHCl3 crystallized from 200 ml isopropanol Colorless crystals with a MP of 100-102° C. were recovered