Home Cart 0 Sign in  
X

[ CAS No. 162166-99-6 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
3d Animation Molecule Structure of 162166-99-6
Chemical Structure| 162166-99-6
Chemical Structure| 162166-99-6
Structure of 162166-99-6 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 162166-99-6 ]

Related Doc. of [ 162166-99-6 ]

Alternatived Products of [ 162166-99-6 ]

Product Details of [ 162166-99-6 ]

CAS No. :162166-99-6 MDL No. :MFCD06795963
Formula : C12H23NO5S Boiling Point : -
Linear Structure Formula :- InChI Key :NEZJCDLNARUJSX-UHFFFAOYSA-N
M.W : 293.38 Pubchem ID :22647269
Synonyms :

Calculated chemistry of [ 162166-99-6 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.92
Num. rotatable bonds : 6
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 76.26
TPSA : 81.29 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.9
Log Po/w (XLOGP3) : 1.28
Log Po/w (WLOGP) : 2.31
Log Po/w (MLOGP) : 1.21
Log Po/w (SILICOS-IT) : 0.38
Consensus Log Po/w : 1.62

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.07
Solubility : 2.5 mg/ml ; 0.00852 mol/l
Class : Soluble
Log S (Ali) : -2.59
Solubility : 0.76 mg/ml ; 0.00259 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.72
Solubility : 5.54 mg/ml ; 0.0189 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.41

Safety of [ 162166-99-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 162166-99-6 ]

* 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.

  • Downstream synthetic route of [ 162166-99-6 ]

[ 162166-99-6 ] Synthesis Path-Downstream   1~85

  • 1
  • [ 124-63-0 ]
  • [ 116574-71-1 ]
  • [ 162166-99-6 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine; In dichloromethane; at 0 - 20℃; [00255] To a solution of <strong>[116574-71-1]tert-butyl 3-(hydroxymethyl)piperidine-1-carboxylate</strong> (1 g, 4.6 mmol) in dichloromethane (20 ml) at 0 OC was added triethylamine (0.97 ml, 7.0 mmol) followed by methanesulfonyl chloride (0.43 ml, 5.6 mmol). The reaction was warmed to room temperature and stirred overnight. The reaction was poured into dichloromethane and washed with saturated sodium bicarbonate solution and brine. The organic layer was dried over magnesium sulfate, filtered, and concentrated to afford the title compound as a viscous oil (1.49 g, yield quantitative) Took into the next reaction without purification.
98% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0℃; for 3h; <strong>[116574-71-1]tert-butyl 3-(hydroxymethyl)piperidin-1-carboxylate</strong> (0.31 g, 1.4 mmol) obtained in Step A was dissolved in 7mL of DCM and cooled to 0C. DIPEA (0.57 mL, 3.3 mmol) and methanesulfonyl chloride (0.12 mL, 1.54 mmol) wereadded thereto, and the mixture was stirred for 3 hours. After addition of water, the reaction solution was extracted withEtOAc to separate an organic layer. The organic layer was dried with MgSO4 to obtain the title compound (0.41 g, 98 %).1H-NMR (CDCl3) delta 4.10 (2H, m), 3.95 (1H, m), 3.80 (1H, m), 3.02 (3H, s), 2.93 (1H, m), 2.79 (1H, m), 1.96 (1H, m), 1.82(1H, m), 1.66 (1H, m), 1.49 (1H, m), 1.45 (9H, s), 1.33 (1H, m)
95% With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 16h; Step 1) Formation of tert-butyl 3-[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate Methanesulfonyl chloride (2.93 g; 25.55 mmol) was added dropwise at 00C to a solution of te/f-butyl 3-(hydroxymethyl)tetrahydro-1 (2/-/)-pyridinecarboxylate (5.0 g; 23.22 mmol) and DIEA (6.0 g; 46.45 mmol) in DCM (80 ml.) and the resulting mixture was stirred for 16 h at RT. The solution was washed with sat. aq. NH4CI (2x) then brine (2x), dried over magnesium sulfate and concentrated in vacuo. Purification by filtration through a short plug of silica (DCM) followed by crystallization from DCM/n- pentane afforded the title compound (6.48 g, 95%) as an off-white solid. 1H NMR(CDCI3, 300 MHz) delta 4.17-4.05 (m, 2H), 3.95 (dd, J = 3.8, 13.2 Hz, 1 H), 3.82 (dt, J = 4.2, 13.2 Hz, 1 H), 3.04 (s, 3H), 2.99-2.88 (m, 1 H), 2.81 (dd, J = 9.3, 13.1 Hz, 1 H), 2.03-1.78 (m, 2H), 1.74-1.62 (m, 1 H), 1.56-1.24 (m, 1 1 H).
93% With triethylamine; In dichloromethane; at 0℃; for 2.83h; Part B: Preparation of 3-Methanesulfonyloxymethyl-piperidine-1-carboxylic Acid Tert-butyl Ester A solution of 3-hydroxymethylpiperidine-1-carboxylic acid tert-butyl ester (15.0 g, 69.7 mmol) and triethylamine (14.6 mL, 104.5 mmol) in dichloromethane (270 mL) was stirred on a bath of ice and acetone. A solution of methanesulfonyl chloride (5.5 mL, 71.1 mmol) in dichloromethane (25 mL) was added dropwise at a rate which kept the internal temperature remained below 0 C. (the addition required about 20 minutes). The mixture was stirred on an ice bath for 2.5 hours, then was concentrated under vacuum. The residue was dissolved in ethyl acetate, and the mixture was filtered to remove a white crystalline solid. The filtrate was concentrated under vacuum to provide an orange gum. Purification by flash chromatography (50% ethyl acetate in hexane) provided a white solid (19.12 g, 93%). 1H NMR (300 MHz, CDC13) delta 4.10 (m, 2H), 3.95 (bd, J=13 Hz, 1H), 3.81 (dt, J=14, 4 Hz, 1H), 3.03 (s, 3H), 2.92 (ddd, J=14, 10, 3 Hz, 1H), 2.79 (dd, J=13, 10 Hz, 1H), 1.97 (m, 1H), 1.83 (m, 1H), 1.68 (m, 1H), 1.49 (m, 1H), 1.46 (s, 9H), 1.30 (m, 1H).
92% With triethylamine; In dichloromethane; at 0℃; for 1h; Triethylamine (1.9 g, 18.6 mmol, 2.0 eq.) and methanesulfonyl chloride (2.12 g, 18.6 mmol, 2.0 eq.) were subsequently added to a solution of <strong>[116574-71-1]tert-butyl 3-(hydroxymethyl)piperidine-1-carboxylate</strong> (2.0 g, 18.6 mmol, 1.0 eq.) in dichloromethane (20 mL) at 0 C. The reaction was stirred at 0 C. for 1 hours, quenched with water (20 mL), then extracted with dichloromethane (10 mL*2). The combined organic phases were dried over anhydrous sodium sulfate, and concentrated to give the title compound (2.5 g, yield: 92%).
88% With triethylamine; In dichloromethane; at 0 - 20℃; for 2h;Inert atmosphere; Step-II : tert-butyl 3-(methylsulfonyloxymethyl)piperidine-l-carboxylate (143)To a solution of compound 142 (30 g, 139 mmol) and triethylamine (29 mL, 208 mmol) in DCM (300 mL) was added Methane sulfonyl chloride (14 mL, 181 mmol) at 0 C under nitrogen atmosphere. It was stirred at room temperature for 2 h. To the reaction mixture Aq.NaHC03 (200 mL) was added and extracted with DCM (2 x 200 mL) followed by washing with brine and organic layer was evaporated to get compound 1 3 (36 g, 88 %) as white solid. 'HNMR (400MHZ, CDCI3): delta 1.25-1.38 (m, 1H), 1.46 (s, 9H), 1.46-1.54 (m, 1H), 1.58-1.70 (m, 1H), 1.79-1.83 (m, 1H), 1.88-2.01 (m, lH), 2.72-2.87 (m, 1H), 2.88-2.97 (m, 1H), 3.03 (s, 3H), 3.78-3.85 (m, 1H), 3.94 (bs, 1H), 4.03-4.16 (m, 2H).
86% With IPr2NEt; In dichloromethane; EXAMPLE 13 Synthesis of 3-Methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester To a solution of 3-hydroxymethyl-piperidine-1-carboxylic acid tert-butyl ester (9.41 g, 0.048 mol) in dichloromethane (200 mL) at room temperature was added iPr2NEt (14.1 g, 0.110 mol), followed by MsCl (5.5 g, 0.048 mol). The reaction mixture was allowed to stir for one hour before concentrating and purifying the resulting residue by silica gel chromatography (1:1 hexane:ethyl acetate). The desired compound was obtained as an oil (11.06 g, 86%).
With triethylamine; In dichloromethane; at 0 - 10℃; for 2 - 5h; N-Boc-3-hydroymethyl piperidine (1 eq), triethylamine (2 eq) were taken in DCM (1Ov). Methane sulfonyl chloride (1.2 eq) was added to the mixture at 0 0C. Mixture was stirred at 10 0C for 2-5 h. Reaction mixture was quenched in water. Organic layer was separated washed with brine, dried over sodium sulfate, filtered, and evaporated in vacuo to get title compound as semi solid.
With triethylamine; at 0 - 10℃; N-Boc-3-hydroymethyI piperidine (1 eq), triethylamine (2 eq) were taken in DCM (10 v). Methane sulfonyl chloride (1.2 eq) was added to the mixture at 0 0C. Mixture was allowed to stirred at 10 0C for 4 h. Reaction mixture was quenched in water. Organic layer was separated washed with brine, dried over sodium sulfate, filtered, and evaporated in vacuo to get title compound as semi solid.
With pyridine; at 20℃; for 48h; A solution of N-Boc-piperidine-3 -methanol (0.25g, 1.16mmol) and methanesulfonyl chloride (2eq) in pyridine (8mL) was stirred at rt for 48h. The mixture was treated with H20 and extracted with dichloromethane. The organic phase was collected, dried using a hydrophobic frit then concentrated in vacuo to give tert-butyl-3-(((methylsulfonyl)oxy)methyl)piperidine- 1-carboxylate.
With triethylamine; In dichloromethane; at 20℃; for 18h; A solution of N-Boc-piperidine-3 -methanol (l .Og, 4.65mmol), triethylamine (2eq) and methanesulfonyl chloride (1.5eq) in dichloromethane (7mL) was stirred at rt for 18h. The resultant mixture was then diluted with dichloromethane and washed with H20 and then brine. The organic phase was collected, dried (MgS04) and concentrated in vacuo to give tert- butyl 3-(((methylsulfonyl)oxy)methyl)piperidine- 1 -carboxylate.
With triethylamine; In tetrahydrofuran; dichloromethane; water; at 0 - 10℃; for 4h; Step 1: 3-Methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester N-Boc-3-hydroymethyl piperidine (1 eq), triethylamine (2 eq) were taken in DCM (10 v). Methane sulfonyl chloride (1.2 eq) was added to the mixture at 0 C. Mixture was allowed to stirred at 10 C. for 4 h. Reaction mixture was quenched in water. Organic layer was separated washed with brine, dried over sodium sulfate, filtered, and evaporated in vacuo to get title compound as semi solid.
23 g With potassium carbonate; In tetrahydrofuran; for 2h;Reflux; 20 g of N-t-butoxycarbonyl-3-hydroxymethylpiperidine was added to 190 ml of tetrahydrofuran,Then add 13g anhydrous potassium carbonate,Then 16 g of methylsulfonyl chloride was added,Heated to reflux, stirred for 2 hours,Add water and ethyl acetate, extract the liquid,Collecting organic phase,Concentration gave 23 g of N-t-butoxycarbonyl-3 - ((methanesulfonyloxy) methyl) piperidine
With triethylamine; In dichloromethane; for 3h;Cooling with ice; The raw material 7 (1.0 eq) was added to the reaction flask, and sufficient DCM was added as a solvent, and the mixture was stirred in an ice bath. After adding Et3N (1.5 eq), methylsulfonyl chloride (1.2 eq) was slowly added dropwise, and the solution was clarified. The mixture was changed to the suspension state, and stirring was continued for 3 hours, and the reaction was monitored by TLC (sulfony), and the reaction was completed. The insoluble matter was removed by filtration, the filtrate was collected, and the filtrate was washed with saturated brine several times by extraction.The oil layer was dried over anhydrous sodium sulfate and the oil layer was evaporated to give an oily product 8 without purification.

  • 2
  • [ 1001665-26-4 ]
  • [ 162166-99-6 ]
  • C29H32ClN5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; 21 EXAMPLE 21 To Intermediate 1-1 (229 mg, 0.682 mmol) was added N-Boc-3-methanesulfonyloxymethyl- piperidine (200 mg, 0.682 mmol), K2CO3 (188 mg, 1.36 mmol), and DMF (3 mL). The reaction was stirred under nitrogen at 1000C for 16 h. The Boc-protected intermediate was isolated by aqueous workup. To the crude intermediate was added 30% TFA/DCM (3 mL), and the reaction was stirred under ambient conditions for 30 min. The deprotection was concentrated in vacuo and purified by reverse-phase HPLC (YMC-Pack Pro C18, 100 x 20 mm, 5μm, gradient 20-100 ACNZH2O with 0.1% TFA) to yield Example 21. LC-MS for C24H24ClN5O [M+H+]: calculated 434.1, found 434.4.
With potassium carbonate In N,N-dimethyl-formamide at 100℃; for 16h; Inert atmosphere; 21 To Intermediate I-1 (229 mg, 0.682 mmol) was added N-Boc-3-methanesulfonyloxymethyl-piperidine (200 mg, 0.682 mmol), K2CO3 (188 mg, 1.36 mmol), and DMF (3 mL). The reaction was stirred under nitrogen at 100° C. for 16 h. The Boc-protected intermediate was isolated by aqueous workup. To the crude intermediate was added 30% TFA/DCM (3 mL), and the reaction was stirred under ambient conditions for 30 min. The deprotection was concentrated in vacuo and purified by reverse-phase HPLC (YMC-Pack Pro C18, 100×20 mm, 5 μm, gradient 20-100 ACN/H2O with 0.1% TFA) to yield Example 21. LC-MS for C24H24ClN5O [M+H+]: calculated 434.1, found 434.4.
  • 3
  • [ 4606-65-9 ]
  • [ 162166-99-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 91 percent / Et3N / dioxane / 2 h 2: Et3N / CH2Cl2
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / acetonitrile; water / 18 h / 0 - 20 °C 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice
Multi-step reaction with 2 steps 1: sodium hydroxide / water; 1,4-dioxane / 5 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 0.25 h / 5 °C / Inert atmosphere 2.2: 16 h / 12 - 20 °C / Inert atmosphere

  • 4
  • [ 24424-99-5 ]
  • [ 162166-99-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 91 percent / Et3N / dioxane / 2 h 2: Et3N / CH2Cl2
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 4 h / 0 - 20 °C / Inert atmosphere 2: triethylamine / dichloromethane / 2 h / 0 - 20 °C / Inert atmosphere
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / acetonitrile; water / 18 h / 0 - 20 °C 2: triethylamine / dichloromethane / 3 h / 0 - 20 °C / Cooling with ice
Multi-step reaction with 2 steps 1: sodium hydroxide / water; 1,4-dioxane / 5 h / 20 °C 2: N-ethyl-N,N-diisopropylamine / dichloromethane / 3 h / 0 °C
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 4 h / 20 °C / Inert atmosphere 2.1: triethylamine / dichloromethane / 0.25 h / 5 °C / Inert atmosphere 2.2: 16 h / 12 - 20 °C / Inert atmosphere

  • 5
  • [ 162166-99-6 ]
  • 2-chlorobenzenesulfonic acid 3-[[1-(aminoiminomethyl)piperidin-3-yl]methoxy]-5-methylphenyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1.) NaH / 1.) DMF, 2.) DMF, 50 deg C, 3 h 2: 4N HCl in dioxane / 2 h 3: Et3N / dimethylformamide / 12 h
  • 6
  • [ 162166-99-6 ]
  • 3-(Azidomethyl)-1-piperidinecarboxylic acid,1,1-dimethylethyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With sodium azide In N,N-dimethyl-formamide at 50℃; for 22h; 1.C Part C: Preparation of 3-Azidomethylpiperidine-1-carboxylic Acid Tert-butyl Ester A solution of 3-methanesulfonyloxymethylpiperidine-1-carboxylic acid tert-butyl ester (19.11 g, 65.1 mmol) in N,N-dimethylformamide (125 mL) was treated with sodium azide (12.70 g, 195 mmol) and the mixture was stirred at 50° C. for 22 hours. The mixture was cooled and filtered, and the filtrate was concentrated under vacuum. The residue was dissolved in ethyl acetate, washed with water, dried over sodium sulfate, and concentrated under vacuum to provide a colorless liquid (15.34 g, 98%) which was used without further purification. 1H NMR (300 MHz, CDC13) δ 3.95 (bd, J=12 Hz, 1H), 3.86 (dt, J=13, 4 Hz, 1H), 3.22 (d, J=7 Hz, 2H), 2.87 (ddd, J=14, 11, 3 Hz, 1H), 2.68 (m, 1H), 1.9-1.6 (3H), 1.49 (m, 1H), 1.47 (s, 9H), 1.26 (m, 1H).
12 g With sodium azide In N,N-dimethyl-formamide for 4h; Reflux; 1.4 (4) Synthesis N-tert-butoxycarbonyl-3- (azidomethyl) piperidine 20 g of N-t-butoxycarbonyl-3 - ((methanesulfonyloxy) methyl) piperidine was added to 200 ml of N, N-dimethylformamide,19 g of sodium azide was added, stirred under reflux for 4 hours,Cooled to room temperature, water and ethyl acetate were added,Extraction and separation, collecting organic phase,Dispensing, drying, concentration,The residue was chromatographed on silica gel to give 12 g of N-tert-butoxycarbonyl-3- (azidomethyl) piperidine.
  • 7
  • [ 116574-71-1 ]
  • [ 162166-99-6 ]
YieldReaction ConditionsOperation in experiment
With trifluoromethylsulfonic anhydride; In 1,1-dichloroethane; Step F Preparation of 3-(methanesulfonyloxymethyl)-N-(tertbutoxycarbonyl)-piperidine 3-Hydroxymethyl-N-(tert-butoxycarbonyl)-piperidine (4.3 g, 20 mmol) was dissolved in dichloroethane (50 mL) with Proton Sponge (6.08 g, 28.3 mmol). Triflic anhydride (4.94 g, 28.4 mmol) was dissolved in dichloroethane (50 mL) and added dropwise to this solution. The reaction was stirred for 3 days, quenched with water (100 mL), the layers separated, and the combined organics washed with 1N HCl, water, bicarbonate, water, and brine. The solution was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 3-(methanesulfonyloxymethyl)-N-(tertbutoxycarbonyl)-piperidine (6 g) as a yellow oil. NMR (CDC13): 1.39, m (1H); 1.42, s (9H); 1.65, m (2H); 1.85, m (2H); 2.77, m (1H); 2.89, t (1H); 2.99, s (3H); 3.81, m (1H); 3.92, m (1H); 4.06, m (2H). Mass Spec (EI): 316.10 (M+Na).
With trifluoromethylsulfonic anhydride; In 1,1-dichloroethane; Step F Preparation of 3-(methanesulfonyloxymethyl)-N-(tertbutoxycarbonyl)-piperidine 3-Hydroxymethyl-N-(tert-butoxycarbonyl)-piperidine (4.3 g, 20 mmol) was dissolved in dichloroethane (50 mL) with Proton Sponge (6.08 g, 28.3 mmol). Triflic anhydride (4.94 g, 28.4 mmol) was dissolved in dichloroethane (50 mL) and added dropwise to this solution. The reaction was stirred for 3 days, quenched with water (100 mL), the layers separated, and the combined organics washed with 1N HCl, water, bicarbonate, water, and brine. The solution was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 3-(methanesulfonyloxymethyl)-N-(tertbutoxycarbonyl)-piperidine (6 g) as a yellow oil. NMR (CDCl3): 1.39, m (1H); 1.42, s (9H); 1.65, m (2H); 1.85, m (2H); 2.77, m (1H); 2.89, t (1H); 2.99, s (3H); 3.81, m (1H); 3.92, m (1H); 4.06, m (2H). Mass Spec (EI): 316.10 (M+Na).
With trifluoromethylsulfonic anhydride; In 1,1-dichloroethane; Step F Preparation of 3-(methanesulfonyloxymethyl)-N-(tertbutoxycarbonyl)-piperidine 3-Hydroxymethyl-N-(tert-butoxycarbonyl)-piperidine (4.3 g, 20 mmol) was dissolved in dichloroethane (50 mL) with Proton Sponge (6.08 g, 28.3 mmol). Triflic anhydride (4.94 g, 28.4 mmol) was dissolved in dichloroethane (50 mL) and added dropwise to this solution. The reaction was stirred for 3 days, quenched with water (100 mL), the layers separated, and the combined organics washed with 1N HCl, water, bicarbonate, water, and brine. The solution was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 3-(methanesulfonyloxymethyl)-N-(tertbutoxycarbonyl)-piperidine (6 g) as a yellow oil. NMR (CDCl3): 1.39, m (1H); 1.42, s (9H); 1.65, m (2H); 1.85, m (2H); 2.77, m (1H); 2.89, t (1H); 2.99, s (3H); 3.81, m (1H); 3.92, m (1H); 4.06, m (2H). Mass Spec (EI): 316.10 (M+Na).
With trifluoromethylsulfonic anhydride; In 1,1-dichloroethane; Step F: Preparation of 3-(methanesulfonyloxymethyl)-N-(tertbutoxycarbonyl)-piperidine 3-Hydroxymethyl-N-(tert-butoxycarbonyl)-piperidine (4.3 g, 20 mmol) was dissolved in dichloroethane (50 mL) with Proton Sponge (6.08 g, 28.3 mmol). Triflic anhydride (4.94 g, 28.4 mmol) was dissolved in dichloroethane (50 mL) and added dropwise to this solution. The reaction was stirred for 3 days, quenched with water (100 mL), the layers separated, and the combined organics washed with 1N HCl, water, bicarbonate, water, and brine. The solution was dried over sodium sulfate, filtered, and concentrated under reduced pressure to afford 3-(methanesulfonyloxymethyl)-N-(tertbutoxycarbonyl)-piperidine (6 g) as a yellow oil. NMR (CDCl3): 1.39, m (1H); 1.42, s (9H); 1.65, m (2H); 1.85, m (2H); 2.77, m (1H); 2.89, t (1H); 2.99, s (3H); 3.81, m (1H); 3.92, m (1H); 4.06, m (2H). Mass Spec (EI): 316.10 (M+Na).

  • 8
  • [ 35386-24-4 ]
  • [ 162166-99-6 ]
  • 3-[4-(2-methoxy-phenyl)-piperazin-1-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
With ammonia; potassium carbonate In ethanol; hexane; ethyl acetate; acetonitrile 14 Synthesis of 3-[4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester EXAMPLE 14 Synthesis of 3-[4-(2-Methoxy-phenyl)-piperazin-1-ylmethyl]-piperidine-1-carboxylic acid tert-butyl ester To a solution of 3-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester (11.06 g, 0.04 mol) in acetonitrile (180 mL) was added potassium carbonate (26 g, 0.19 mol) followed by 1-(2-methoxy-phenyl) piperazine (7.25 g, 0.04 mol). After completion of addition the reaction mixture was heated to reflux. After 12 h the reaction mixture was cooled down to room temperature and quenched with water. The aqueous layer was extracted with ethyl acetate (3*100 mL). The combined organic layers were dried over sodium sulfate and concentrated to yield an oil. This crude material was purified using silica gel chromatography (7:3:0.05 Hexane:EtOAc:2M NH3 in EtOH) to afford the desired compound in good yield (8.0 g, 55%). C22H35N3O3,LRMS (m/z)=390 (MH+).
  • 9
  • [ 533-31-3 ]
  • [ 162166-99-6 ]
  • C18H25NO5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In N,N-dimethyl acetamide
  • 10
  • [ 183802-98-4 ]
  • [ 162166-99-6 ]
  • C17H23BrClNO3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In N,N-dimethyl acetamide
  • 11
  • [ 150-76-5 ]
  • [ 162166-99-6 ]
  • C18H27NO4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In N,N-dimethyl acetamide
  • 12
  • [ 162166-99-6 ]
  • [ 108-95-2 ]
  • [ 405087-03-8 ]
YieldReaction ConditionsOperation in experiment
With sodium hydride In N,N-dimethyl acetamide
  • 13
  • [ 586372-76-1 ]
  • [ 162166-99-6 ]
  • [ 586372-93-2 ]
YieldReaction ConditionsOperation in experiment
18% Stage #1: 4-(benzyloxy)-3-bromopyridin-2(1H)-one With sodium hexamethyldisilazane In tetrahydrofuran; N,N-dimethyl-formamide for 1h; Stage #2: 3-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 75℃; Stage #3: With hydrogenchloride In 1,4-dioxane for 3h; 28 To the material of Example 11 (3.1 g, 0. 011 mol) in DMF (20 mL) was added dropwise sodium bis (trimethylsilyl) amide (1M in THF, 12 mL). Contents were stirred one hour before adding dropwise a solution OF 3-METHANESULFONYLOXYMETHYL-1-PIPERIDINE-1- carboxylic acid tert-butyl ester (BIOORG. Med. CLZEM. Lett, 8 (13), 1998,1595-1600) (4.2 g, 0.015 mol) in DMF (5 mL). Contents were heated at 75°C overnight. Contents were allowed to cool, poured into water (100 mL) and a solid was filtered. The solid was stirred in 4 N HCL/DIOXANE (15 mL) for 3 hours and filtered to give the desired as a white solid, 752 mg (18% yield). mp 138.1-139. 2°C. FABHRMS m/z 377.0859 (M+H, C18H22BRN202 requires 377. 0865). 1H NMR (DMSO-d6/300 MHz): 9.50-9. 10 (br, 2H); 8.00 (d, 1H) ; 7.50-7. 30 (m, 5H) ; 6.93 (d, 1H) ; 5.30 (s, 2H); 4.30-3. 90 (m, 3H); 3.40-3. 10 (m, 3H); 2.80-2. 50 (m, 3H); 2.40-2. 00 (m, 1H) ; 1.90-1. 60 (m, 4H); 1.40-1. 10 (m, 1H). Anal. Calcd for CL8H21BRN202 (2HC1, 0.25 H2O) : C, 47.55 ; H, 5.21 ; N, 6.16. Found: C, 47.48 ; H, 5.46 ; N, 6.27.
  • 14
  • [ 67-56-1 ]
  • [ 162166-99-6 ]
  • [ 868065-26-3 ]
YieldReaction ConditionsOperation in experiment
With sodium at 10℃; for 3h; Heating / reflux; 2 Sodium metal (3 eq) was dissolved in dry methanol (10 v) and 3-methanesulfonyloxy methyl-piperidine-1-carboxylic acid ter t-buty ester (1 eq) was added to this stirred solution at 10 0C. Mixture was refluxed form 3h. Mixture was quenched in water. Product was extracted by EtOAc. Organic layer was washed with water, brine, dried over sodium sulfate, filtered and evaporated in vacuo to afforded title compound as liquid.
With sodium at 10℃; Reflux; 8.2 Sodium metal (3 eq) was dissolved in dry methanol (10 v) and 3-methanesulfonyloxy methyl-piperidine-l-carboxylic acid /erf-butyl ester (1 eq) was added to this stirred solution at 10 0C. Mixture was refluxed form 3h. Mixture was quenched in water.Product was extracted by EtOAc. Organic layer was washed with water, brine, dried over sodium sulfate, filtered and evaporated in vacuo to afford title compound as liquid.
  • 15
  • [ 67-63-0 ]
  • [ 162166-99-6 ]
  • [ 1244059-18-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: isopropyl alcohol; 3-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester With sodium hydride at 20℃; for 72h; Stage #2: With water; ammonium chloride In ethyl acetate 78.2 Step 2) Formation of tert-butyl 3-(isopropoxymethyl)piperidine-1-carboxylate Sodium hydride (0.25 g; 10.2 mmol) was added portionwise to a solution of fe/f-butyl3-[(methylsulfonyl)oxy]methyl}piperidine-1-carboxylate (1.5 g; 5.11 mmol) in isopropanol (20 ml.) and the resulting mixture was stirred at RT for 3 days. The solution was diltued with EtOAc, washed with sat. aq. NH4CI and water, dried over magnesium sulfate and concentrated in vacuo. Purification by filtration through a short plug of silica (EtOAc/c-hexane, 1/1 ) afforded the title compound (1.4 g, quantitative yield) as yellow oil. 1H NMR (DMSOd6, 300 MHz) δ 4.13 - 3.61 (m, 2H), 3.54 - 3.42 (m, 1 H), 3.26 - 3.12 (m, 2H), 2.84 - 2.713 (m, 1 H), 1.72 - 1.48 (m, 3H), 1.38 (s, 9H), 1.35 - 1.1 1 (m, 3H), 1.07 (d, J = 5.9 Hz, 6H).
  • 16
  • [ 162166-99-6 ]
  • [ 1346161-56-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 80 °C 2: trifluoroacetic acid / 2 h / 20 °C
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3: hydrogenchloride / 1,4-dioxane; isopropyl alcohol / 1 h / 140 °C / Microwave
  • 17
  • [ 162166-99-6 ]
  • [ 1346162-24-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
  • 18
  • [ 162166-99-6 ]
  • [ 1346161-72-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 80 °C 2: trifluoroacetic acid / 2 h / 20 °C 3: triethylamine / dichloromethane / 0.5 h / 20 °C
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C 2: trifluoroacetic acid / dichloromethane / 2 h / 20 °C 3: hydrogenchloride / 1,4-dioxane; isopropyl alcohol / 1 h / 140 °C / Microwave 4: triethylamine / dichloromethane / 0.5 h / 20 °C
  • 19
  • [ 23002-51-9 ]
  • [ 162166-99-6 ]
  • [ 1346162-23-9 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 16h; A suspension of 6-chloro-lH-pyrazol[3,4-d]pyrimidine (0.12g, 0.78mmol), tert-butyl-3- (((methylsulfonyl)oxy)methyl)piperidine- 1-carboxylate (leq) and potassium carbonate (2eq) in DMF (3mL) was stirred at rt for 16h. The mixture was treated with H20 and extracted with dichloromethane. The organic phase was collected, dried using a hydrophobic frit then concentrated in vacuo to give tert-butyl-3-((6-chloro-lH-pyrazolo[3,4-d]pyrimidin-l- yl)methyl)piperidine- 1 -carboxylate .
  • 20
  • [ 1296307-10-2 ]
  • [ 162166-99-6 ]
  • [ 1346162-32-0 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 18h; 21 A suspension of intermediate A (200mg, 0.93mmol), potassium carbonate (2eq) and tert-butyl 3-(((methylsulfonyl)oxy)methyl)piperidine-l-carboxylate (leq) in DMF (2mL) was stirred at 80°C for 18h. After cooling to rt, the mixture was diluted with EtOAc and washed with H20 and then brine. The organic phase was collected, dried (MgS04) and concentrated in vacuo. The resultant residue was purified by column chromatography (petroleum ether: EtOAc) to give tert-butyl 3 -((6-(( 1 -methyl- 1 H-pyrazol-4-yl)amino)- 1 H-pyrazo lo [3 ,4-d]pyrimidin- 1 - yl)methyl)piperidine- 1 -carboxylate
  • 21
  • [ 162166-99-6 ]
  • [ 688809-97-4 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium / methanol / 3 h / 10 °C 2: hydrogenchloride / 1,4-dioxane / 1 h / 0 - 5 °C
  • 22
  • [ 162166-99-6 ]
  • [ 868065-26-3 ]
YieldReaction ConditionsOperation in experiment
With sodium In methanol at 10℃; for 3h; Step 2.: 3-Methoxymethyl-piperidine-1-carboxylic acid tert-butyl esterSodium metal (3 eq) was dissolved in dry methanol (10 v) and 3-methanesulfonyloxy methyl-piperidine-1-carboxylic acid tert-butyl ester (1 eq) was added to this stirred solution at 10° C. Mixture was refluxed form 3 h. Mixture was quenched in water. Product was extracted by EtOAc. Organic layer was washed with water, brine, dried over sodium sulfate, filtered and evaporated in vacuo to afford title compound as liquid.
  • 23
  • [ 371-41-5 ]
  • [ 162166-99-6 ]
  • [ 1309206-94-7 ]
YieldReaction ConditionsOperation in experiment
79% With caesium carbonate In N,N-dimethyl-formamide at 60℃; for 6h; Inert atmosphere; 34.III Step-III : tert-butyl 3-[(4-fluorophenoxy)methyl]piperidine-l-carboxylate (144)To a solution of compound 143 (3 g, 10.2 mmol) and Cs2C03 (10 g, 30.6 mmol) in DMF (25 mL) was added 4-fluorophenol (1.37 mL, 12.2 mmol) at room temperature under nitrogen atmosphere. It was stirred at 60 °C for 6 h. Reaction mixture was diluted with water (200 mL) and extracted with ethylacetate (2 x 100 mL) followed by washing with brine and organic layer was evaporated to get compound 144 (2.5 g, 79 %) as oil.
  • 24
  • [ 106-48-9 ]
  • [ 162166-99-6 ]
  • tert-butyl 3-((4-chlorophenoxy)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% With caesium carbonate In dichloromethane at 75℃; for 3h; 56 Preparation 56: tert-butyl 3-((4-chlorophenoxy)methyl)piperidine- 1-carboxylate [00256] To a solution of tert-butyl 3-(((methylsulfonyl)oxy)methyl)piperidine-1- carboxylate (510 mg, 1.7 mmol) in dimethylformamide (8 ml) was added 4-chlorophenol (330 mg, 2.6 mmol) followed by cesium carbonate (1.7 g, 5.2 mmol). The reaction was heated to 75 OC. After 3h, the reaction was cooled to room temperature and left at room temperature for 36 h. The reaction mixture was poured into water and extracted with 30% ethyl acetate in hexanes. The organic layer was dried over magnesium sulfate, filtered, and concentrated. Purified by column chromatography eluting with 0-10% ethyl acetate in hexanes to give the title compound as a colorless oil (367 mg, yield 65%).
  • 25
  • [ 162166-99-6 ]
  • 3-((4-chlorophenoxy)methyl)piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: caesium carbonate / dichloromethane / 3 h / 75 °C 2: trifluoroacetic acid / dichloromethane / 20 °C
  • 26
  • [ 162166-99-6 ]
  • (3-((4-chlorophenoxy)methyl)piperidin-1-yl)(3-(furan-2-yl)phenyl)methanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: caesium carbonate / dichloromethane / 3 h / 75 °C 2: trifluoroacetic acid / dichloromethane / 20 °C 3: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / tetrahydrofuran
  • 27
  • N-(tert-butyloxycarbonyl)nipecotic acid [ No CAS ]
  • [ 162166-99-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: methanol / 24 h / 20 °C 2: sodium tetrahydroborate / ethanol / 20 °C 3: potassium carbonate / tetrahydrofuran / 2 h / Reflux
Multi-step reaction with 2 steps 1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / 0 °C 2: triethylamine / dichloromethane / 1 h / 0 °C
  • 28
  • [ 162166-99-6 ]
  • (1-acryloylpiperidin-3-yl)methyl methanesulfonate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: hydrogenchloride / ethyl acetate; water / 1 h / 0 - 20 °C 2: triethylamine / dichloromethane / 1 h / 0 °C
  • 29
  • [ 162166-99-6 ]
  • 3,4-dimethyl-7-(piperidin-3-ylmethoxy)-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; caesium carbonate / N,N-dimethyl-formamide / 72 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C
  • 30
  • [ 162166-99-6 ]
  • (±)-3,4-dimethyl-7-[(N-methylpiperidin-3-yl)methoxy]-2H-chromen-2-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; caesium carbonate / N,N-dimethyl-formamide / 72 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 3: potassium carbonate / acetone / 6 h / 20 °C
  • 31
  • [ 162166-99-6 ]
  • (±)-3,4-dimethyl-7-[(N-benzylpiperidin-3-yl)methoxy]-2H-chromen-2-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; caesium carbonate / N,N-dimethyl-formamide / 72 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 3: potassium carbonate / acetone / 0.5 h / 130 °C / Microwave irradiation
  • 32
  • [ 162166-99-6 ]
  • (±)-3,4-dimethyl-7-[(N-(3-chlorobenzyl)piperidin-3-yl)methoxy]-2H-chromen-2-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; caesium carbonate / N,N-dimethyl-formamide / 72 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 3: potassium carbonate / acetone / 0.5 h / 130 °C / Microwave irradiation
  • 33
  • [ 162166-99-6 ]
  • (±)-7-[1-(3-bromobenzyl)piperidin-3-yl]methoxy}-3,4-dimethyl-2H-chromen-2-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; caesium carbonate / N,N-dimethyl-formamide / 72 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 3: potassium carbonate / acetone / 0.5 h / 130 °C / Microwave irradiation
  • 34
  • [ 162166-99-6 ]
  • (±)-3,4-dimethyl-7-[(N-(4-fluorobenzyl)piperidin-3-yl)methoxy]-2H-chromen-2-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; caesium carbonate / N,N-dimethyl-formamide / 72 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 3: potassium carbonate / acetone / 0.5 h / 130 °C / Microwave irradiation
  • 35
  • [ 162166-99-6 ]
  • (±)-3,4-dimethyl-7-[(N-(4-chlorobenzyl)piperidin-3-yl)methoxy]-2H-chromen-2-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; caesium carbonate / N,N-dimethyl-formamide / 72 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 3: potassium carbonate / acetone / 0.5 h / 130 °C / Microwave irradiation
  • 36
  • [ 162166-99-6 ]
  • (±)-3,4-dimethyl-7-[(N-(4-(methylsulfonyl)benzyl)piperidin-3-yl)-methoxy]-2H-chromen-2-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; caesium carbonate / N,N-dimethyl-formamide / 72 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 3: potassium carbonate / acetone / 0.5 h / 130 °C / Microwave irradiation
  • 37
  • [ 162166-99-6 ]
  • (±)-4-[(3-((3,4-dimethyl-2H-2-oxochromen-7-yl)oxymethyl)-piperidin-1-yl)methyl]benzonitrile hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; caesium carbonate / N,N-dimethyl-formamide / 72 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 3: potassium carbonate / acetone / 0.5 h / 130 °C / Microwave irradiation
  • 38
  • [ 162166-99-6 ]
  • (±)-7-((1-(3,4-dimethoxybenzyl)piperidin-3-yl)methoxy)-3,4-dimethyl-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; caesium carbonate / N,N-dimethyl-formamide / 72 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 1.25 h / 0 - 20 °C 3: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere
  • 39
  • [ 2107-78-0 ]
  • [ 162166-99-6 ]
  • tert-butyl 3-[(3,4-dimethyl-2-oxo-2H-chromen-7-yl)oxy]methyl}piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
9% With caesium carbonate; triethylamine In N,N-dimethyl-formamide at 70℃; for 72h;
  • 40
  • [ 162166-99-6 ]
  • 1-(3-((4-amino-3-(2-fluoro-4-(2,3,5,6-tetrafluorophenoxy)phenyl)-1H-pyrazolo[3,4-d]pyrimidin-1-yl) methyl)piperidin-1-yl)prop-2-en-1-one hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: hydrogenchloride / ethyl acetate; water / 1 h / 0 - 20 °C 2: triethylamine / dichloromethane / 1 h / 0 °C 3: caesium carbonate / N,N-dimethyl-formamide
  • 41
  • [ 162166-99-6 ]
  • piperidin-3-ylmethyl methanesulfonate hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With hydrogenchloride In water; ethyl acetate at 0 - 20℃; for 1h; C piperidin-3-ylmethyl methanesulfonate hydrochloride 4M HCl/EtOAc (10 mL) was added to a solution of tert-butyl 3-((methylsulfonyloxy)methyl)piperidine-1-carboxylate (2.5 g, 8.5 mmol) in ethyl acetate (40 mL) at 0° C. The reaction mixture was stirred at room temperature for 1 h and concentrated to give the title compound hydrochloride (1.93 g, yield: 98%).
  • 42
  • [ 162166-99-6 ]
  • 5-methyl-1-((1-(4-phenoxybenzyl)piperidin-3-yl)methyl)pyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 3.2: 72 °C 4.1: trifluoroacetic acid / 72 °C / Inert atmosphere
  • 43
  • [ 162166-99-6 ]
  • C32H35N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 3: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere
  • 44
  • [ 162166-99-6 ]
  • C32H35N3O4 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 3.1: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 3.2: 72 °C
  • 45
  • [ 162166-99-6 ]
  • 3-((Benzyloxy)methyl)-5-methyl-1-(piperidin-3-ylmethyl)pyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C
  • 46
  • [ 162166-99-6 ]
  • 5-methyl-1-((1-(3-phenoxybenzyl)piperidin-3-yl)methyl)pyrimidine-2,4(1H,3H)-dione [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: potassium carbonate / N,N-dimethyl-formamide / 80 °C 2: trifluoroacetic acid / dichloromethane / 3 h / 20 °C 3: sodium tris(acetoxy)borohydride / 1,2-dichloro-ethane / 20 °C / Inert atmosphere 4: trifluoroacetic acid / 72 °C / Inert atmosphere
  • 47
  • [ 119451-90-0 ]
  • [ 162166-99-6 ]
  • C24H33N3O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate In N,N-dimethyl-formamide at 80℃; 4 4.4.2. General procedure for synthesis of compound 32, 33, 37 and 38 General procedure: A suspension of 3-((benzyloxy)methyl)-5-methylpyrimidine-2,4(1H,3H)-dione (20, 1 equiv), N-Boc-protected mesylates (1.1-2 equiv), potassium carbonate (1.5-2 equiv) was stirred at 80 °C overnight (compound 37 and 38) or 24 h (compound 32 and 33) under argon. The work-up procedure as well as the second step were performed as has been described for the synthesis of compound 34.
  • 48
  • [ 148763-41-1 ]
  • [ 162166-99-6 ]
  • 49
  • [ 162166-99-6 ]
  • 3-(azidomethyl)piperidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 4 h / Reflux 2: hydrogenchloride / dichloromethane / 5 h / 20 °C
  • 50
  • [ 162166-99-6 ]
  • C10H13BrN6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: sodium azide / N,N-dimethyl-formamide / 4 h / Reflux 2: hydrogenchloride / dichloromethane / 5 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 6 h / Reflux
  • 51
  • [ 162166-99-6 ]
  • (1-(5-bromopyrimidin-2-yl)piperidin-3-yl)methanamine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: sodium azide / N,N-dimethyl-formamide / 4 h / Reflux 2: hydrogenchloride / dichloromethane / 5 h / 20 °C 3: potassium carbonate / N,N-dimethyl-formamide / 6 h / Reflux 4: borane-THF / tetrahydrofuran / 16 h / 20 °C
  • 52
  • [ 773837-37-9 ]
  • [ 162166-99-6 ]
  • [ 948015-72-3 ]
YieldReaction ConditionsOperation in experiment
93% In N,N-dimethyl-formamide; at 60℃; for 16.0h; tert-butyl 3-(methylsulfonyloxymethyl)piperidin-1-carboxylate (0.41 g, 1.4 mmol) obtained in Step B was dissolvedin 7 mL of DMF. Sodium cyanide (0.075 g, 1.54 mmol) was added thereto, and the mixture was stirred at 60Cfor 16 hours. The reaction solution was concentrated under reduced pressure, diluted with water, and extracted withEtOAc. The organic layer was separated and dried with MgSO4 to obtain the title compound (0.29 g, 93 %).1H-NMR (CDCl3) delta 3.90 (1H, m), 3.82 (1H, m), 2.92 (2H, m), 2.30 (2H, m), 1.92 (2H, m), 1.68 (1H, m), 1.49 (1H, m),1.46 (9H, s), 1.35 (1H, m)
  • 53
  • [ 162166-99-6 ]
  • 2-[1-[5-(6-isopropylsulfanyl-2-pyridyl)-2-pyridyl]-3-piperidyl]acetonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 16 h / 60 °C 2: hydrogenchloride / 1,4-dioxane; dichloromethane / 1 h / 0 °C 3: caesium carbonate / N,N-dimethyl-d<SUB>6</SUB>-formamide / 4 h / 50 °C
  • 54
  • [ 162166-99-6 ]
  • 2-[1-[5-(6-isopropylsulfanyl-2-pyridyl)-2-pyridyl]-3-piperidyl]acetic acid [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 16 h / 60 °C 2: hydrogenchloride / 1,4-dioxane; dichloromethane / 1 h / 0 °C 3: caesium carbonate / N,N-dimethyl-d<SUB>6</SUB>-formamide / 4 h / 50 °C 4: sodium hydroxide / water; ethanol / 16 h / Reflux
  • 55
  • [ 162166-99-6 ]
  • 2-(3-piperidyl)acetonitrile hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 16 h / 60 °C 2: hydrogenchloride / 1,4-dioxane; dichloromethane / 1 h / 0 °C
  • 56
  • [ 162166-99-6 ]
  • tert-butyl 3-((chlorosulfonyl)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 12 h / 95 °C 2: chlorine / dichloromethane; water / 0 - 5 °C
  • 57
  • [ 162166-99-6 ]
  • tert-butyl 3-((fluorosulfonyl)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 12 h / 95 °C 2: chlorine / dichloromethane; water / 0 - 5 °C 3: 18-crown-6 ether; potassium fluoride / acetonitrile / 0.16 h / 20 °C
  • 58
  • [ 162166-99-6 ]
  • 3-((fluorosulfonyl)methyl)piperidinium chloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: N,N-dimethyl-formamide / 12 h / 95 °C 2: chlorine / dichloromethane; water / 0 - 5 °C 3: 18-crown-6 ether; potassium fluoride / acetonitrile / 0.16 h / 20 °C 4: hydrogenchloride / dichloromethane; 1,4-dioxane / 16 h / 0 - 20 °C
  • 59
  • [ 162166-99-6 ]
  • [ 10387-40-3 ]
  • tert-butyl 3-((acetylthio)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
85% In N,N-dimethyl-formamide at 95℃; for 12h;
  • 60
  • [ 1133065-96-9 ]
  • [ 162166-99-6 ]
  • [ 1338227-13-6 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: 3,4-dihydropyrazino[1,2-b]indazol-1(2H)-one With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: 3-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil Reflux; Inert atmosphere;
  • 61
  • [ 1133065-98-1 ]
  • [ 162166-99-6 ]
  • [ 1338227-15-8 ]
YieldReaction ConditionsOperation in experiment
75% Stage #1: 2,3,4,5-tetrahydro-1H-[1,4]diazepino[1,2-b]indazol-1-one With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: 3-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil Reflux; Inert atmosphere;
  • 62
  • [ 272-49-1 ]
  • [ 162166-99-6 ]
  • C18H25N3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% Stage #1: 1H-pyrrolo[3,2-b]pyridine With sodium hydride In N,N-dimethyl-formamide; mineral oil at 20℃; for 0.5h; Stage #2: 3-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester In N,N-dimethyl-formamide; mineral oil at 20℃; PREPARATION OF INTERMEDIATE 68 Sodium hydride (19.1 mg, 0.48 mmol, 60%> dispersion in mineral oil) was added portionwise to a solution of 4-azaindole (CAS: 272-49-1; 52 mg, 0.44 mmol) in DMF (4.12 mL) at rt. The resulting mixture was stirred at rt for 30 min. Then tert-butyl 3-(((methylsulfonyl)oxy)methyl)piperidine-l-carboxylate (CAS: 162166-99-6; 0.1 g, 0.34 mmol) was added and the mixture was further stirred at rt overnight. The mixture was poured in to ice and EtOAc was added. The organic layer was separated, washed with brine, dried over MgS04, filtered and concentrated in vacuo. The residue thus obtained was purified by flash column chromatography (silica; MeOH in DCM, 0/100 to 10/90) and the desired fractions were concentrated in vacuo to yield intermediate 68 as colorless oil (63 mg, 58% yield).
  • 63
  • [ 162166-99-6 ]
  • C13H17N3*ClH [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C 1.2: 20 °C 2.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C
  • 64
  • [ 162166-99-6 ]
  • C19H23N5OS [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 20 °C 1.2: 20 °C 2.1: hydrogenchloride / 1,4-dioxane / 1 h / 20 °C 3.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.08 h / 20 °C 3.2: 16 h / 20 °C
  • 65
  • [ 162166-99-6 ]
  • 7-(piperidin-3-ylmethoxy)-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: triethylamine; caesium carbonate / N,N-dimethyl-formamide / 72 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 0 - 20 °C
  • 66
  • [ 162166-99-6 ]
  • 7-[1-(3-hydroxypropyl)piperidin-3-yl]methoxy}-2H-chromen-2-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: triethylamine; caesium carbonate / N,N-dimethyl-formamide / 72 h / 70 °C 2: trifluoroacetic acid / dichloromethane / 0 - 20 °C 3: potassium carbonate; potassium iodide / acetonitrile / Reflux
  • 67
  • [ 93-35-6 ]
  • [ 162166-99-6 ]
  • tert-butyl 3-[(2-oxo-2H-chromen-7-yl)oxy]methyl}piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
81% With caesium carbonate; triethylamine In N,N-dimethyl-formamide at 70℃; for 72h; 6.1.8. General procedure for the synthesis of substituted tert-butyl4-[(2-oxo-2H-chromen-7-yl)oxy]alkyl}piperidine-1-carboxylate(7b-e) and tert-outyl 3-[(2-oxo-2H-chromen-7-yl)oxy]methyl}piperidine-1-carboxylate (7g) General procedure: By following a previously reported method [28], a mixture of theappropriate 7-hydroxycoumarin (7.0 mmol), the suitable mesylateester (6.7 mmol), triethylamine (2.8 mL, 20 mmol) and cesiumcarbonate (2.3 g, 7.0 mmol) were heated in dry DMF (15 mL) at70 C for 72 h. Then the mixture was poured onto crushed ice. Thefiltratewas collected and washed with abundant water yielding the desired Boc-protected intermediates 7b-e, 7g that were deprotectedwithout further purification.
  • 68
  • [ 162166-99-6 ]
  • [ 5188-07-8 ]
  • tert-butyl 3-((methylsulfinyl)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
In ethanol at 20℃; for 6h; 35 Preparation 35: Methyl(methylimino)(piperidin-3-ylmethyl)-λ-sulfanone, A35. NaSMe (4.06 g, 58 mmol) was added to a solution of tert-butyl 3- (methylsulfonyloxymethyl)piperidine-1-carboxylate (8.5 g, 29 mmol) in EtOH (170 mL). The mixture was stirred at ambient temperature for 6 hours then concentrated in vacuo. The residue was partitioned between DCM and saturated aqueous NaHCO3 solution, and the organic phase separated, dried and concentrated in vacuo. The residue was purified by column chromatography (silica, MeOH/DCM gradient elution) to give a pale yellow oil (6.9 g). This material was dissolved in DCM (100 mL), the solution cooled in an ice bath and mCPBA (6.93 g of 70% pure w/w, 28 mmol) was added portionwise. After the addition was complete, the reaction mixture was stirred for 10 minutes then partitioned between DCM, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium thiosulfate solution. The organic phase was dried and concentrated in vacuo. The residue was purified by column chromatography (silica, DCM/MeOH gradient elution) to give tert-butyl 3-((methylsulfinyl)methyl)piperidine-1-carboxylate (5.5 g, 72% over two steps) as a colourless oil.
Stage #1: 3-methanesulfonyloxymethyl-piperidine-1-carboxylic acid tert-butyl ester; sodium thiomethoxide In ethanol at 20℃; for 6h; Stage #2: With 3-chloro-benzenecarboperoxoic acid In dichloromethane for 0.166667h; 10 Preparation 10: [00382] Sodium thiomethoxide (4.06 g, 58 mmol) was added to a solution of tert-butyl 3- (methylsulfonyloxymethyl)piperidine-1-carboxylate (8.5 g, 29 mmol) in ethanol (170 mL). The mixture was stirred at ambient temperature for 6 hours then concentrated in vacuo. The residue was partitioned between DCM and saturated aqueous NaHCO3 solution. The organic phase was dried and concentrated in vacuo. The residue was purified by chromatography (silica, MeOH/DCM gradient elution) to give a pale yellow oil (6.9 g). This material was dissolved in DCM (100 mL) and the solution cooled in an ice bath. m-CPBA (6.93 g of 70% pure w/w, 28 mmol) was added portionwise. After addition was complete the reaction mixture was stirred for 10 minutes then partitioned between DCM, saturated aqueous sodium bicarbonate solution and saturated aqueous sodium thiosulfate solution. The organic phase was dried and concentrated in vacuo. The residue was purified by chromatography (silica, DCM/MeOH gradient elution) to give the product as a colourless oil.
  • 69
  • [ 162166-99-6 ]
  • imino(methyl)(piperidin-3-ylmethyl)-λ6-sulfanone [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: ethanol / 6 h / 20 °C 2.1: [bis(acetoxy)iodo]benzene; magnesium oxide; dirhodium tetraacetate / dichloromethane / 20 °C 2.2: 72 h / 20 - 50 °C 3.1: trifluoroacetic acid / dichloromethane / 20 °C
Multi-step reaction with 3 steps 1.1: ethanol / 6 h / 20 °C 1.2: 0.17 h 2.1: 2,2,2-trifluoroacetamide; [bis(acetoxy)iodo]benzene; magnesium oxide; dirhodium tetraacetate / dichloromethane / 16 h / 20 °C / Inert atmosphere 3.1: trifluoroacetic acid / dichloromethane / 16 h / 20 °C
  • 70
  • [ 162166-99-6 ]
  • tert-butyl 3-((S-methylsulfonimidoyl)methyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: ethanol / 6 h / 20 °C 2.1: [bis(acetoxy)iodo]benzene; magnesium oxide; dirhodium tetraacetate / dichloromethane / 20 °C 2.2: 72 h / 20 - 50 °C
Multi-step reaction with 2 steps 1.1: ethanol / 6 h / 20 °C 1.2: 0.17 h 2.1: 2,2,2-trifluoroacetamide; [bis(acetoxy)iodo]benzene; magnesium oxide; dirhodium tetraacetate / dichloromethane / 16 h / 20 °C / Inert atmosphere
  • 71
  • [ 162166-99-6 ]
  • [ 193629-39-9 ]
YieldReaction ConditionsOperation in experiment
With lithium bromide; In acetone;Reflux; Raw material 8 (1.0 eq) was added to the reaction flask, and a sufficient amount of ACE was added as a solvent. The mixture was stirred at room temperature, and LiBr (3.0 eq) was slowly added thereto, and the temperature was gradually raised to reflux, overnight. The reaction solution was cooled to room temperature, and the reaction mixture was quenched with water. The reaction mixture was evaporated to dryness, and then the mixture was evaporated and evaporated with EtOAc and water, and the oil layer was collected, and the oil layer was washed three times with saturated brine, and the oil layer was dried over Na 2 SO 4 Product 9, no purification required.
  • 72
  • [ 162166-99-6 ]
  • [ 948015-72-3 ]
YieldReaction ConditionsOperation in experiment
327 mg With sodium cyanide In dimethyl sulfoxide at 100℃; for 2.5h; 1 tert-butyl 3-(cyanomethyl)piperidine-1-carboxylate (37) 15The compound 36 (542 mg, 1.84 mmol, 1 eq) and NaCN (135 mg, 2.76 mmol, 1.5 eq) are dissolved in 6.4 mL DMSO, and then heated at 100 C for 2.5 hours. After cooling down, it is diluted with Et2O, washed with water, brine, dried over Na2SO4. Filtration and concentration afford the crude cyanide 61 (327 mg, 79%) slightly yellow oil, which is used in the next step without further purifications. 1H NMR (400 MHz, Chloroform-d) d 3.92 (d, J = 13.2 Hz, 1H), 3.81 (dt, J = 13.5, 4.4 Hz, 1H), 2.91 (ddd, J = 13.5, 10.3, 3.2 Hz, 1H), 2.83-2.67 (m, 1H), 2.30 (qd, J = 16.9, 6.6 Hz, 2H), 1.90 (dddq, J = 19.9, 9.9, 6.5, 3.8, 3.3 Hz, 2H), 1.67 (ddt, J = 12.6, 8.2, 4.2 Hz, 1H), 1.56-1.48 (m, 1H), 1.45 (s, 9H), 1.43-1.23 (m, 1H). HRMS (ESI) : m/z [M+H]+ calcd. for C12H21N2O2: 225.15 found: 225.16
  • 73
  • [ 203661-82-9 ]
  • [ 162166-99-6 ]
  • benzyl 4-(4-[[1-(tert-butoxycarbonyl)piperidin-3-yl]methoxy]phenyl)piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
63.9% With potassium carbonate In N,N-dimethyl-formamide at 85℃; for 3h; Step 1: of benzyl 4-(4-[[1-(tert-butoxycarbonyl)piperidin-3- yl]methoxy]phenyl)piperidine-1-carboxylate Into a 100-mL round-bottom flask, was placed benzyl 4-(4- hydroxyphenyl)piperidine-1-carboxylate (1.37 g, 4.400 mmol, 1.00 equiv), Dimethyl Formamide (15 mL), K2CO3 (1.82 g, 13.199 mmol, 3 equiv), tert-butyl 3- [(methanesulfonyloxy)methyl]piperidine-1-carboxylate (1.55 g, 5.283 mmol, 1.20 equiv). The resulting solution was stirred for 3 h at 85 in an oil bath. The reaction was then quenched by the addition of water (20 mL). The resulting solution was extracted with ethyl acetate (2x20 mL). The resulting mixture was washed with brine (2 x20 mL). The mixture was dried over anhydrous sodium sulfate. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1/1). The collected fractions were combined and concentrated under vacuum. This resulted in 1.43 g (63.9%) of benzyl 4-(4-[[1-(tert-butoxycarbonyl)piperidin-3- yl]methoxy]phenyl)piperidine-1-carboxylate as a yellow solid. MS (ES+): m/z 531.30 [MH+].
  • 74
  • [ 162166-99-6 ]
  • [ 301185-41-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 85 °C 2: dimethyl sulfoxide / 16 h / 35 °C
  • 75
  • 2-fluoro-4-(5-methanesulfonylbenzooxazol-2-yl)phenol [ No CAS ]
  • [ 162166-99-6 ]
  • 3-[2-fluoro-4-(5-methanesulfonylbenzooxazol-2-yl)phenoxymethyl]piperidine-1-carboxylic acid t-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.3% With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 16h; 30 [Example 30] Preparation of 3-[2-fluoro-4-(5-methanesulfonyl-benzooxazol-2-yl)-phenoxymethyl]-piperidine-1-carboxylic acid t-butyl ester The compound (0.1 g, 0.33 mmol) prepared in Example 25 step 1 and 3-methanesulfonyloxymethyl-piperidine-1-carboxylic acid t-butyl ester (0.14 g, 0.49 mmol) were mixed with N,N-dimethylform After dissolving in amide (5 ml), potassium carbonate (0.14 g, 0.98 mmol) was added thereto. The reaction mixture was reacted at 80° C. for 16 hours and acid-treated with 1N hydrochloric acid. The acid-treated reaction mixture was extracted with ethyl acetate to separate the organic layer, and the separated organic layer was dried over anhydrous sodium sulfate, concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1). Thus, the title compound (0.13 g 79.3%) was obtained.
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 162166-99-6 ]

Amides

Chemical Structure| 161975-39-9

[ 161975-39-9 ]

tert-Butyl 4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

Similarity: 0.97

Chemical Structure| N/A

[ N/A ]

(trans-4-(((tert-butoxycarbonyl)(ethyl)amino)methyl)cyclohexyl)methyl methanesulfonate

Similarity: 0.97

Chemical Structure| 929301-95-1

[ 929301-95-1 ]

tert-Butyl 4-(2-((methylsulfonyl)oxy)ethyl)-4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

Similarity: 0.97

Chemical Structure| 405090-66-6

[ 405090-66-6 ]

tert-Butyl 3-(2-((methylsulfonyl)oxy)ethyl)piperidine-1-carboxylate

Similarity: 0.97

Chemical Structure| 274692-06-7

[ 274692-06-7 ]

(S)-tert-Butyl 3-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

Similarity: 0.96

Sulfonates

Chemical Structure| 161975-39-9

[ 161975-39-9 ]

tert-Butyl 4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

Similarity: 0.97

Chemical Structure| N/A

[ N/A ]

(trans-4-(((tert-butoxycarbonyl)(ethyl)amino)methyl)cyclohexyl)methyl methanesulfonate

Similarity: 0.97

Chemical Structure| 929301-95-1

[ 929301-95-1 ]

tert-Butyl 4-(2-((methylsulfonyl)oxy)ethyl)-4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

Similarity: 0.97

Chemical Structure| 405090-66-6

[ 405090-66-6 ]

tert-Butyl 3-(2-((methylsulfonyl)oxy)ethyl)piperidine-1-carboxylate

Similarity: 0.97

Chemical Structure| 274692-06-7

[ 274692-06-7 ]

(S)-tert-Butyl 3-(((methylsulfonyl)oxy)methyl)pyrrolidine-1-carboxylate

Similarity: 0.96

Related Parent Nucleus of
[ 162166-99-6 ]

Piperidines

Chemical Structure| 161975-39-9

[ 161975-39-9 ]

tert-Butyl 4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

Similarity: 0.97

Chemical Structure| 929301-95-1

[ 929301-95-1 ]

tert-Butyl 4-(2-((methylsulfonyl)oxy)ethyl)-4-(((methylsulfonyl)oxy)methyl)piperidine-1-carboxylate

Similarity: 0.97

Chemical Structure| 405090-66-6

[ 405090-66-6 ]

tert-Butyl 3-(2-((methylsulfonyl)oxy)ethyl)piperidine-1-carboxylate

Similarity: 0.97

Chemical Structure| 147699-19-2

[ 147699-19-2 ]

tert-Butyl 4-(2-((methylsulfonyl)oxy)ethyl)piperidine-1-carboxylate

Similarity: 0.96

Chemical Structure| 1958100-64-5

[ 1958100-64-5 ]

tert-Butyl 4-(3-((methylsulfonyl)oxy)cyclobutyl)piperidine-1-carboxylate

Similarity: 0.92