79099-07-3

Basic information

• Product Name: N-(tert-Butoxycarbonyl)-4-piperidone
• Synonyms: BOC-4-PIPERIDONE;BOC-PPD;BOC-PIPERIDONE;1-BOC-PIPERIDIN-4-ONE;1-BOC-4-PIPERIDINONE;1-BOC-4-PIPERIDONE;1-N-BOC-4-PIPERIDONE;N-Boc-4-piperidone, tert-Butyl 4-oxo-1-piperidinecarboxylate
• CAS NO: 79099-07-3
• Molecular Formula: C₁₀H₁₇NO₃
• Molecular Weight: 199.25
• EINECS: 1308068-626-2
• Product Categories: Piperidines;Amino Acids & Derivatives;Pyrans, Piperidines & Piperazines;Amines;blocks;Carbonyl Compounds;Heterocycles;Miscellaneous Biochemicals;pharmacetical;Pyrans, Piperidines &Piperazines;Piperidine;Piperidine Series
• Mol File: 79099-07-3.mol
• Article Data: 137

Chemical Properties

• Melting Point: 73-77 °C(lit.)
• Boiling Point: 336.77°C (rough estimate)
• Flash Point: 129.1 ºC
• Appearance: White to slightly yellow/Crystalline Powder
• Density: 1.1249 (rough estimate)
• Vapor Pressure: 0.00215mmHg at 25°C
• Refractive Index: 1.4610 (estimate)
• Storage Temp.: Store at 0-5°C
• Solubility: Methanol
• PKA: -1.58±0.20(Predicted)
• Water Solubility: slightly soluble
• BRN: 3650236
• CAS DataBase Reference: N-(tert-Butoxycarbonyl)-4-piperidone(CAS DataBase Reference)
• NIST Chemistry Reference: N-(tert-Butoxycarbonyl)-4-piperidone(79099-07-3)
• EPA Substance Registry System: N-(tert-Butoxycarbonyl)-4-piperidone(79099-07-3)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 36/38-22-36/37/38-20/21/22
• Safety Statements: 37/39-26-36-24/25
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 79099-07-3(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 79099-07-3 differently. You can refer to the following data:
1. 1-t-Boc-4-piperidone is a compound useful in organic synthesis.
2. 1-Boc-4-piperidone is used as a pharmaceutical intermediate. It is involved in the preparation of 1-piperidin-4-yl-substituted butyro- and valerolactams.
3. 1-t-Boc-4-piperidone is a compound useful in organic synthesis used in the preparation of (aminoaryl)(benzyloxy)pyridines as potential antitumor agents.

Chemical Properties

Light Yellow Powder

Application

N-(tert-Butoxycarbonyl)-4-piperidone is a chemical intermediate that belongs to the group of p2. It is an ancillary used in the synthesis of many organic compounds, including epidermal growth factor analogs. It has been shown to have pharmacokinetic properties that are similar to those of epidermal growth factor and can be used for the treatment of cancer. This drug has been shown to inhibit the growth of skin cancer cells and may also be useful in treating other types of cancer.

InChI:InChI=1/C10H17NO3/c1-10(2,3)14-9(13)11-6-4-8(12)5-7-11/h4-7H2,1-3H3

Synthetic route

di-tert-butyl dicarbonate (24424-99-5) + 4-piperidone hydrochloride (41979-39-9) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With sodium hydrogencarbonate In water 1) 35 deg C, 1 h; 2) 50 deg C, 2.5 h;	100%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 16h;	100%
Stage #1: di-tert-butyl dicarbonate; 4-piperidone hydrochloride With triethylamine; dmap In methanol at 20℃; for 20h; Stage #2: With hydrogenchloride In dichloromethane	100%

di-tert-butyl dicarbonate (24424-99-5) + piperidine-4,4-diol hydrochloride (40064-34-4) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With sodium carbonate In tetrahydrofuran; water at 20℃; for 12h;	99%
With sodium hydroxide In tetrahydrofuran; water at 20℃; for 16h;	98.6%
With potassium hydrogencarbonate In chloroform at 20℃;	95%

4-piperidinone monohydrate (73390-11-1) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With sodium hydrogencarbonate In water at 50℃; for 3h;	99%

di-tert-butyl dicarbonate (24424-99-5) + piperidin-2-one hydrochloride (5174-67-4) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With dmap; N-ethyl-N,N-diisopropylamine In acetonitrile for 2h; Inert atmosphere;	99%

tert-butyl carbamate (4248-19-5) + 4-piperidone hydrochloride (41979-39-9) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
Stage #1: 4-piperidone hydrochloride With sodium hydroxide In water at 0℃; Stage #2: tert-butyl carbazate In water for 4h;	98.44%

piperidin-4-one (41661-47-6) + tert-butyl (3-cyano-4,6-dimethylpyridin-2-yl) carbonate → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
In ethanol for 1h; Reflux;	96%

piperidin-4-one (41661-47-6) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With triethylamine In methanol; dichloromethane at 0 - 25℃; for 12h; Inert atmosphere;	95%
With triethylamine In dichloromethane at 20℃; for 16h;	86%
With sodium hydroxide In tetrahydrofuran for 2h; Ambient temperature;

t-butyl 4-hydroxy piperidine-1-carboxylate (109384-19-2) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With bis(1,5-cyclooctadiene)nickel(0); potassium tert-butylate; 1,3-bis[2,6-diisopropylphenyl]imidazolium chloride In 2,4-dichlorotoluene at 25℃; for 0.5h; Inert atmosphere;	95%
With sodium hypochlorite; C186H204N12O36; sodium hydrogencarbonate; potassium bromide In dichloromethane; water at 0 - 15℃; for 4h; pH=8.6;	95%
With (diacetoxyiodo)benzene In dichloromethane at 20℃; for 3h;	95%

di-tert-butyl dicarbonate (24424-99-5) + 4-piperidone monohydrochloride monohydrate (40064-34-4) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane; water for 12h; Cooling with ice;	94%
With sodium hydroxide In 1,4-dioxane	92.5%
With triethylamine In dichloromethane; ethyl acetate	86%

t-butyl malonate (541-16-2) + piperidine-4,4-diol hydrochloride (40064-34-4) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With triethylamine In tetrahydrofuran; water at 0 - 20℃;	93%

di-tert-butyl dicarbonate (24424-99-5) + piperidin-4-one hydrochloride monohydrate → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With sodium hydroxide In 1,4-dioxane	93%
With triethylamine In dichloromethane at 20℃;	88%
With sodium carbonate In 1,4-dioxane; water at 20℃; for 1h;	87%
With sodium carbonate In 1,4-dioxane; water at 20℃; for 1h;	87%

5-tert-butoxycarbonyl-3-hydroxy-4,5,6,7-tetrahyroisoxazolo<4,3-c>pyridine (152559-29-0) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With hydrogen; platinum on activated charcoal In ethanol Ambient temperature;	86%

1-phenylmethyl-4-piperidone (3612-20-2) + di-tert-butyl dicarbonate (24424-99-5) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With PMHS; palladium dihydroxide In ethanol at 20℃; for 5h;	86%

4-piperidone monohydrochloride monohydrate (40064-34-4) + S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine (41840-28-2) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With triethylamine In 1,4-dioxane; water for 6h; Ambient temperature;	81.3%

S-tert-butoxycarbonyl-4,6-dimethyl-2-mercaptopyrimidine (41840-28-2) + piperidine-4,4-diol hydrochloride (40064-34-4) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With triethylamine In 1,4-dioxane; water at 20℃; for 6h;	81.3%

tert-butyl 4-((diphenoxyphosphoryl)oxy)-3,6-dihydropyridine-1(2H)-carboxylate (856684-31-6) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With triethylsilane; cyclohexa-1,4-diene; oxygen; cobalt acetylacetonate In methanol; nonane at 24℃; under 760.051 Torr; Reagent/catalyst;	81%

tert-butyldicarbonate (34619-03-9) + 4-piperidone hydrochloride (41979-39-9) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With triethylamine In methanol at 20℃; for 2h;	75%
With triethylamine In dichloromethane at 0 - 20℃;	71%

tert-butyl formate (762-75-4) + piperidin-4-one hydrochloride monohydrate → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 16h; Inert atmosphere;	73%

tert-butyl 4-methylidenepiperidine-1-carboxylate (159635-49-1) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With 2,6-dimethylpyridine; sodium periodate; ruthenium(III) chloride trihydrate In dichloromethane; water; acetonitrile at 20℃; for 1h; Inert atmosphere;	71%

3-(1-(tert-butoxycarbonyl)piperidin-4-yl)propanoic acid (154775-43-6) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With (2,2'-dipyridyl)bis(5-methyl-2-(4-fluoro)phenylpyridine-N,C)iridium(III) hexafluorophosphate; oxygen; sodium carbonate; 1,1'-diethyl-4,4'-bipyridinium diperchlorate In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 16h; Irradiation;	68%

N-[(tert-butoxy)carbonyl]piperidine-4-carboxylic acid (84358-13-4) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With (2,2'-dipyridyl)bis(5-methyl-2-(4-fluoro)phenylpyridine-N,C)iridium(III) hexafluorophosphate; oxygen; sodium carbonate; 1,1'-diethyl-4,4'-bipyridinium diperchlorate In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 16h; Irradiation;	67%

2-(1-(tert-butoxycarbonyl)piperidin-4-yl)acetic acid (157688-46-5) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With (2,2'-dipyridyl)bis(5-methyl-2-(4-fluoro)phenylpyridine-N,C)iridium(III) hexafluorophosphate; oxygen; sodium carbonate; 1,1'-diethyl-4,4'-bipyridinium diperchlorate In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 16h; Irradiation;	63%

tert butyl 4-formylpiperidine-1-carboxylate (137076-22-3) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With (2,2'-dipyridyl)bis(5-methyl-2-(4-fluoro)phenylpyridine-N,C)iridium(III) hexafluorophosphate; oxygen; sodium carbonate; 1,1'-diethyl-4,4'-bipyridinium diperchlorate In dimethyl sulfoxide at 20℃; under 760.051 Torr; for 16h; Irradiation;	17%

tert-butyl 4-methoxypiperidine-1-carboxylate (188622-27-7) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
With calcium hypochlorite; acetic acid In water; acetonitrile at 0℃; regioselective reaction;	3%

4-HYDROXYPIPERIDINE (5382-16-1) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / tetrahydrofuran; H2O / 1 h / 20 °C 2: SO3*NMe3; triethylamine; DMSO / 18 h / 20 °C View Scheme
Multi-step reaction with 2 steps 1: CH2Cl2 / 1 h / 20 °C 2: tetrapropylammoniumperruthenate; NMO; 3 Angstroem molecular sieves / CH2Cl2 / 1 h View Scheme
Multi-step reaction with 2 steps 1: sodium carbonate / tetrahydrofuran; water / 0 - 20 °C 2: Dess-Martin periodane / dichloromethane / 2 h / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium carbonate / tetrahydrofuran; water / 0 - 20 °C 2: Dess-Martin periodane / dichloromethane / 0 - 20 °C View Scheme
Multi-step reaction with 2 steps 1: sodium hydroxide; water / 1,4-dioxane / 0 - 20 °C 2: pyridinium chlorochromate; SiO2 / dichloromethane / 2 h / 20 °C View Scheme

di-tert-butyl dicarbonate (24424-99-5) + 1.) NaH; 2.) SOCl2 → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: NaOH / tetrahydrofuran; H2O / 1 h / 20 °C 2: SO3*NMe3; triethylamine; DMSO / 18 h / 20 °C View Scheme

di-tert-butyl dicarbonate (24424-99-5) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
Multi-step reaction with 2 steps 1: CH2Cl2 / 1 h / 20 °C 2: tetrapropylammoniumperruthenate; NMO; 3 Angstroem molecular sieves / CH2Cl2 / 1 h View Scheme
Multi-step reaction with 3 steps 1: 96 percent / NaCO3, NaCl / CHCl3; H2O / 12 h / Heating 2: 59 percent / NaOH, NH2OH*HCl / H2O / 1 h / 0 °C 3: 86 percent / H2 / 10percent Pt/C / ethanol / Ambient temperature View Scheme
With triethylamine In diethyl ether; dichloromethane

ethyl 4-piperidone-3-carboxylate hydrochloride (4644-61-5) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
Multi-step reaction with 3 steps 1: 96 percent / NaCO3, NaCl / CHCl3; H2O / 12 h / Heating 2: 59 percent / NaOH, NH2OH*HCl / H2O / 1 h / 0 °C 3: 86 percent / H2 / 10percent Pt/C / ethanol / Ambient temperature View Scheme

ethyl 1-benzyl-4-oxopiperidine-3-carboxylate hydrochloride (1454-53-1) → N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3)

Conditions	Yield
Multi-step reaction with 4 steps 1: 99 percent / H2 / 10percent Pd/C / ethanol; H2O / 24 h / 2280 Torr / Ambient temperature 2: 96 percent / NaCO3, NaCl / CHCl3; H2O / 12 h / Heating 3: 59 percent / NaOH, NH2OH*HCl / H2O / 1 h / 0 °C 4: 86 percent / H2 / 10percent Pt/C / ethanol / Ambient temperature View Scheme

diazoacetic acid ethyl ester (623-73-4) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 5-oxo-azepane-1,4-dicarboxylic acid 1-tert-butyl ester 4-ethyl ester (141642-82-2)

Conditions	Yield
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one With boron trifluoride diethyl etherate In diethyl ether at -30 - -25℃; for 0.333333h; Stage #2: diazoacetic acid ethyl ester In diethyl ether at -30 - 20℃;	100%
With boron trifluoride diethyl etherate In diethyl ether at -25℃; for 1h; Inert atmosphere;	99%
Stage #1: diazoacetic acid ethyl ester; N-tert-butyloxycarbonylpiperidin-4-one With boron trifluoride diethyl etherate In diethyl ether at 0℃; for 2h; Stage #2: With sodium carbonate In diethyl ether; water at 0℃;	98%

diethyl 1-cyanomethylphosphonate (2537-48-6) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 4-(cyanomethylidene)piperidine-1-carboxylic acid tert-butyl ester

Conditions	Yield
With lithium hexamethyldisilazane In tetrahydrofuran at -70℃; for 0.666667h; Inert atmosphere;	100%
With lithium hexamethyldisilazane In tetrahydrofuran at -70℃; for 0.666667h; Inert atmosphere;	100%
With lithium bromide In tetrahydrofuran at 20℃; for 3h; Inert atmosphere;	100%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + 2-amino-phenol (95-55-6) → 1-(tert-butoxycarbonyl)-4-[(2-hydroxyphenyl)amino]piperidine (162045-48-9)

Conditions	Yield
	100%
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one; 2-amino-phenol With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 120℃; for 0.0833333h; Microwave irradiation; Stage #2: With water; sodium hydrogencarbonate	75%
With sodium tris(acetoxy)borohydride

chloro-trimethyl-silane (75-77-4) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → tert-butyl 4-[(trimethylsilyl)oxy]-3,6-dihydropyridine-1(2H)-carboxylate (211108-48-4)

Conditions	Yield
With triethylamine In N,N-dimethyl-formamide Inert atmosphere;	100%
With sodium hydrogencarbonate; triethylamine In N,N-dimethyl-formamide at 90℃; for 21h; Inert atmosphere;	99%
With triethylamine In N,N-dimethyl-formamide at 0 - 90℃;	99%

morpholine (110-91-8) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 4-morpholin-4-yl-3,6-dihydro-2H-pyridine-1-carboxylic acid ter-tbutyl ester (217807-98-2)

Conditions	Yield
toluene-4-sulfonic acid In benzene for 24h; Heating / reflux;	100%
With toluene-4-sulfonic acid In toluene Reflux;	100%
With toluene-4-sulfonic acid In toluene for 16h; Reflux; Inert atmosphere;	100%

diethoxyphosphoryl-acetic acid ethyl ester (867-13-0) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → tert-butyl 4-(2-ethoxy-2-oxoethylidene)piperidine-1-carboxylate (135716-08-4)

Conditions	Yield
With sodium hydride In tetrahydrofuran at 20℃; for 1h; Horner-Emmons reaction;	100%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0℃; for 0.5h; Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In tetrahydrofuran at 20℃; for 22h;	100%
Stage #1: diethoxyphosphoryl-acetic acid ethyl ester With sodium hydride In tetrahydrofuran at 0 - 5℃; for 0.5h; Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In tetrahydrofuran at 0 - 20℃; for 2h;	100%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → t-butyl 4-hydroxy piperidine-1-carboxylate (109384-19-2)

Conditions	Yield
With sodium tetrahydroborate In ethanol	100%
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one With sodium tetrahydroborate In ethanol at 0 - 20℃; for 4h; Stage #2: With water; ammonium chloride In ethanol	100%
With sodium hydroxide; sodium borohydrid In methanol	100%

pyrrolidine (123-75-1) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → N-tert-butoxycarbonyl-4-(tetrahydropyrrole-1-yl)-1,2,3,6-tetrahydropyridine (207691-65-4)

Conditions	Yield
With toluene-4-sulfonic acid In toluene for 20h; Heating;	100%
In toluene for 6h; Heating / reflux;	100%
In toluene at 90℃; for 3h; Dean-Stark;	100%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + ethylamine (75-04-7) → 4-(N-ethylamino)-1-tert-butoxycarbonylpiperidine (264905-39-7)

Conditions	Yield
With hydrogen; platinum on carbon In ethanol; water at 50℃; under 1500.15 Torr; for 4h;	100%
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran; 1,2-dichloro-ethane at 20℃; for 24h; Inert atmosphere;	99%
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one; ethylamine With acetic acid In tetrahydrofuran for 0.0833333h; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran for 24h;	94%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + 1-amino-2-propene (107-11-9) → 1-(t-butoxycarbonyl)-4-(N-prop-2-enyl)aminopiperidine (235420-68-5)

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;	100%
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 0 - 20℃;	95%
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃;
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 20℃;
With sodium tris(acetoxy)borohydride; acetic acid In tetrahydrofuran at 20℃;

formaldehyd (50-00-0) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + benzylamine (100-46-9) → 7-benzyl-9-oxo-3,7-diazabicyclo[3.3.1]nonane-3-carboxylic acid tert-butyl ester (227940-70-7)

Conditions	Yield
With acetic acid In methanol for 4h; Heating / reflux;	100%
With acetic acid In methanol Reflux;	100%
With acetic acid In methanol for 5h; Reflux;	100%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + propan-1-ol-3-amine (156-87-6) → tert-butyl 4-[(3-hydroxypropyl)amino]piperidine-1-carboxylate (864655-26-5)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In ethanol under 3361.55 Torr; for 1.5h;	100%
With hydrogen; palladium on activated charcoal In methanol at 20℃; under 760.051 Torr; for 24h;	99%
With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane for 2h;
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one; propan-1-ol-3-amine With acetic acid In dichloromethane at 20 - 27℃; for 3h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20 - 27℃; Inert atmosphere;

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + benzylamine (100-46-9) → 4-benzylamino-piperidine-1-carboxylic acid tert-butyl ester (206273-87-2)

Conditions	Yield
With sodium tris(acetoxy)borohydride In dichloromethane; acetic acid at 20℃;	100%
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one; benzylamine With acetic acid In dichloromethane at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In dichloromethane at 20℃; for 16h;	100%
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 16h;	98%

1-indoline (496-15-1) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → tert-butyl 4-(indolin-1-yl) piperidine-1-carboxylate (400828-91-3)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 0 - 65℃; for 65h; Product distribution / selectivity;	100%
With sodium tris(acetoxy)borohydride; acetic acid at 0 - 25℃; for 1h; Product distribution / selectivity;	100%
Stage #1: 1-indoline; N-tert-butyloxycarbonylpiperidin-4-one With acetic acid In 1,2-dichloro-ethane at 0℃; for 0.166667h; Stage #2: With sodium tris(acetoxy)borohydride In 1,2-dichloro-ethane at 10 - 20℃; for 65h; Product distribution / selectivity;	100%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + 4-methoxyphenyl magnesium bromide (13139-86-1) → tert-butyl 4-hydroxy-4-(4-methoxyphenyl)-1-piperidinecarboxylate (302924-67-0)

Conditions	Yield
In diethyl ether at 0 - 20℃; for 2h;	100%
In diethyl ether at 0 - 20℃; for 2h;	100%
In diethyl ether at 0 - 20℃; for 2h;	100%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + 5-nitroindole (6146-52-7) → tert-butyl 4-(5-nitro-1H-indol-3-yl)-5,6-dihydropyridine-1(2H)-carboxylate (151273-41-5)

Conditions	Yield
With pyrrolidine In ethanol at 20℃; for 72h; Heating / reflux;	100%
With sodium methylate In methanol for 24h; Reflux;	87%
With pyrrolidine In ethanol at 20℃; for 72h;	80%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + ethyl 2-cyanoacetate (105-56-6) → tert-butyl 4-(1-cyano-2-ethoxy-2-oxoethylidene)-4-piperidine-1-carboxylate (193537-11-0)

Conditions	Yield
With ammonium acetate; acetic acid; benzene	100%
With ammonium acetate; acetic acid In benzene for 4h; Reflux; Inert atmosphere;	99%
With ammonium acetate In acetic acid; benzene for 4h; Heating / reflux;	99%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + ethanolamine (141-43-5) → tert-butyl 4-[(2-hydroxyethyl)amino]piperidine-1-carboxylate (701298-37-5)

Conditions	Yield
With hydrogen; palladium on activated charcoal In methanol at 20℃; under 760.051 Torr; for 24h;	100%
With hydrogen; palladium 10% on activated carbon In ethanol under 3361.55 Torr; for 1.5h;	100%
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one; ethanolamine With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; Inert atmosphere; Stage #2: With sodium hydroxide In dichloromethane; water pH=10;	94%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + N,N-dimethyl-formamide dimethyl acetal (4637-24-5) → t-butyl-3-[(dimethylamino)methylidene]-4-oxopiperidine-1-carboxylate (157327-41-8)

Conditions	Yield
In N,N-dimethyl-formamide at 80℃; for 24h;	100%
In N,N-dimethyl-formamide at 80℃; for 24h;	100%
at 95℃; for 1.5h;	94.4%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + cyanoacetic acid amide (107-91-5) → tert-butyl 2-amino-3-carbamoyl-4,5-dihydrothieno[2,3-c]pyridine-6(7H)-carboxylate (1001020-08-1)

Conditions	Yield
With morpholine; sulfur In ethanol at 20℃;	100%
With morpholine; sulfur In ethanol for 4h; Gewald Aminoheterocycles Synthesis; Reflux; Inert atmosphere;	95%
With sulfur; diethylamine In ethanol at 20℃;	93%

2-methoxy-5-bromopyridine (13472-85-0) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 4-(2-methoxy-5-pyridinyl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (850141-84-3)

Conditions	Yield
With n-butyllithium In tetrahydrofuran at -78 - 20℃; for 12h;	100%
Stage #1: 2-methoxy-5-bromopyridine With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.0833333h; Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In tetrahydrofuran; hexanes at -78 - 0℃;	44%
With n-butyllithium In diethyl ether; hexane at -78 - 20℃;	42%
Stage #1: 2-methoxy-5-bromopyridine With n-butyllithium In diethyl ether; hexane at -78℃; for 0.5h; Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In diethyl ether; hexane at -78 - 25℃;	42%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → piperidin-4-one (41661-47-6)

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 3h;	100%
With trifluoroacetic acid In dichloromethane at 20℃;	100%
With trifluoroacetic acid In dichloromethane
With trifluoroacetic acid In 1,2-dichloro-ethane
With hydrogenchloride In 1,4-dioxane at 20℃; for 4h;	6.5 g

meta-fluoroaniline (372-19-0) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → tert-butyl 4-((3-fluorophenyl)amino)piperidine-1-carboxylate (679409-18-8)

Conditions	Yield
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃;	100%
With sodium tris(acetoxy)borohydride; acetic acid In dichloromethane at 20℃; for 2h; Cooling with ice;	98.1%
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 0 - 20℃; for 2h;	91%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + cyclopropanemethylamine (2516-47-4) → 4-(cyclopropylmethylamino)piperidine-1-carboxylic acid tert-butyl ester (710973-92-5)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In tetrahydrofuran under 2068.65 Torr; for 1h;	100%
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 20℃; Acidic conditions;	74%
With sodium tris(acetoxy)borohydride; acetic acid In 1,2-dichloro-ethane at 25℃;
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one; cyclopropanemethylamine With sodium acetate; acetic acid In tetrahydrofuran at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran at 20℃; for 15h; Stage #3: With hydrogenchloride In diethyl ether; water
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one; cyclopropanemethylamine With sodium acetate; acetic acid In tetrahydrofuran at 20℃; for 1h; Stage #2: With sodium tris(acetoxy)borohydride In tetrahydrofuran for 15h; Stage #3: With sodium hydroxide; water

1-amino-3-methylbutane (107-85-7) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → 4-(3-methyl-butylamino)-piperidine-1-carboxylic acid tert-butyl ester (710974-71-3)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In ethanol under 3102.97 Torr;	100%
With hydrogen; palladium 10% on activated carbon In ethanol under 3102.97 Torr;	100%
With hydrogen; palladium on activated carbon In ethanol under 3102.97 Torr;	100%
With hydrogen; palladium on activated carbon In ethanol under 3102.97 Torr;	100%
With sodium tris(acetoxy)borohydride In dichloromethane at 20℃;

2,2-dimethylpropylamine (5813-64-9) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → tert-butyl 4-[(2,2-dimethylpropyl)amino]piperidine-1-carboxylate (710976-87-7)

Conditions	Yield
With hydrogen; palladium 10% on activated carbon In ethanol under 3102.97 Torr; for 3h;	100%
Stage #1: 2.2-dimethylpropylamine; N-tert-butyloxycarbonylpiperidin-4-one With triethylamine; zinc(II) chloride In methanol at 65℃; for 6h; Stage #2: With sodium cyanoborohydride In methanol at 0 - 25℃; for 17h;	88%
With sodium tetrahydroborate In methanol at 0 - 20℃; for 42h;

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → tert-butyl 4-(hydroxyimino)piperidine-1-carboxylate (150008-24-5)

Conditions	Yield
With hydroxylamine hydrochloride; sodium hydroxide In ethanol; water for 0.5h; Reflux;	100%
With hydrogenchloride; hydroxylamine In ethanol for 1.5h; Reflux;	100%
With hydroxylamine hydrochloride; sodium acetate In methanol; water Reflux;	100%

N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) + methylamine (74-89-5) → 4-methylamino-piperidine-1-carboxylic acid tert-butyl ester (147539-41-1)

Conditions	Yield
Stage #1: N-tert-butyloxycarbonylpiperidin-4-one; methylamine In methanol for 1h; pH=5 - 6; Stage #2: With methanol; sodium cyanoborohydride for 12h; Cooling with ice;	100%
With formic acid; palladium 10% on activated carbon; hydrogen In ethanol at 50℃; under 30003 Torr; Autoclave;	99%
With formic acid; palladium 10% on activated carbon; hydrogen In ethanol at 50℃; under 30003 Torr; Autoclave;	99%

carbon tetrabromide (558-13-4) + N-tert-butyloxycarbonylpiperidin-4-one (79099-07-3) → tert-butyl 4-(dibromomethylidene)piperidine-1-carboxylate (305794-65-4)

Conditions	Yield
With triphenylphosphine In dichloromethane at 0 - 20℃; for 72h; Inert atmosphere;	100%
With triphenylphosphine In acetonitrile at 0 - 25℃; for 2.25h;	56%
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0 - 20℃; for 0.5h; Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In dichloromethane at -78 - 20℃;
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0 - 20℃; Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In dichloromethane at -78 - 20℃;
Stage #1: carbon tetrabromide With triphenylphosphine In dichloromethane at 0 - 20℃; Stage #2: N-tert-butyloxycarbonylpiperidin-4-one In dichloromethane at -78 - 20℃;

Upstream product

• 41661-47-6 piperidin-4-one 
• 24424-99-5 di-tert-butyl dicarbonate 
• 41979-39-9 4-piperidone hydrochloride 
• 40064-34-4 piperidine-4,4-diol hydrochloride 
• 40064-34-4 4-piperidone monohydrochloride monohydrate 
• 144-55-8 sodium hydrogencarbonate 
• 34619-03-9 tert-butyldicarbonate 
• 123-91-1 1,4-dioxane 
• 77-92-9 citric acid 
• 180160-77-4 6-Chloro-3-(1,2,3,6-Tetrahydro-4-pyridinyl)-1H-indole 
• 74-88-4 methyl iodide 
• 345235-81-6 6-chloro-3-(1-tert-butoxycarbonyl-1,2,3,6-tetrahydropyridin-4-yl)-1H-indole 
• 95798-23-5 1-(benzyloxycarbonyl)-4-hydroxypiperidine 
• 4248-19-5 tert-butyl carbazate 

Downstream Products

• 235109-63-4 4-(4-chloro-phenyl)-4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester 
• 138647-49-1 4-Trifluoromethanesulfonyloxy-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester 
• 173469-30-2 4-<4-(4-hydroxy-1-tert-butoxycarbonyl)piperidyl>-(1H)-imidazole 
• 169206-55-7 2-oxo-1-oxa-3,8-diazaspiro<4.5>decane-8-carboxylic acid tert-butyl ester 
• 185843-79-2 4-(3,5-dibromophenyl)-4-hydroxy-1-tert-butyloxycarbonylpiperidine 
• 205813-90-7 4-(2-Bromo-phenylimino)-piperidine-1-carboxylic acid tert-butyl ester 
• 118652-88-3 3-bromo-piperidin-4-one-hydrobromide 
• 188869-05-8 tert-butyl 3-bromo-4-oxo-piperidine-1-carboxylate 
• 213769-24-5 4-Hydroxy-4-(2-mercaptomethyl-phenyl)-piperidine-1-carboxylic acid tert-butyl ester 
• 191327-95-4 tert-butyl 4-(2-fluorobenzyl)-4-hydroxypiperidine-1-carboxylate 
• 220741-33-3 4-(4-benzyloxy-phenylamino)-piperidine-1-carboxylic acid tert-butyl ester 
• 177948-41-3 1-tert-Butyloxycarbonyl-4-[(R)-1-(4-fluorophenyl)-2-methoxyethyl]aminopiperidine 
• 182144-07-6 4-{1-[4-(4-methoxy-benzenesulfonyl)-phenyl]-vinyl}-[1,4']bipiperidinyl-1'-carboxylic acid tert-butyl ester 
• 177948-45-7 1-(tert-butyloxycarbonyl)4-(2-phenylpiperidin-1-yl)piperidine 

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