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

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)
• Refractive Index: 1.4610 (estimate)
• Storage Temp.: Store at 0-5°C
• 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

Chemical Properties

Light Yellow Powder

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

• 107-95-9 beta-Alanine 
• 124-41-4 Sodium methanolate 
• 24424-99-5 Di-tert-butyl dicarbonate 
• 67-56-1 Methanol 
• 96-33-3 Methyl acrylate 

Downstream Products

• 790999-57-4 Glycine, N-(2,3,3-trimethylbicyclo[2.2.1]hept-2-yl)- (9CI) 
• 790999-92-7 4-METHOXYPHENYL 3,4-O-ISOPROPYLIDENE-6-O-(4-METHYLBENZOYL)-BETA-D-GALACTOPYRANOSIDE 
• 791000-45-8 Benzoic acid, 3,4,5-trimethoxy-, 1-(4-morpholinylmethyl)-2-(6,7,8-trimethoxy-4-oxo-2-propyl-3(4H)-quinazolinyl)ethyl ester 
• 791000-51-6 2-Furanamine, N,N-dimethyl-5-[[(4-nitrophenyl)imino]methyl]- 
• 791000-96-9 2-(4-NITRO-PHENYL)-OXAZOL-4-YL-METHYLAMINE 
• 791001-11-1 1,3,5-Triazine-2,4(1H,3H)-dione, 6-[(3-hydroxyphenyl)amino]- (9CI) 
• 791001-51-9 Phenol, 6-(aminomethyl)-2,4-dichloro-3-methyl- (9CI) 
• 79100-16-6 METHYL 2-(2-FORMYL-1H-PYRROL-1-YL)BENZOATE 
• 79100-20-2 5,6-dichloro-1,3-dihydro-2H-imidazo[4,5-b]pyrazin-2-one 
• 791002-11-4 Benzofuro[2,3-b]pyridinium, 1-ethyl-2-[3-(1-ethyl-2(1H)-quinolinylidene)-1-propenyl]- (9CI) 
• 79100-21-3 1,3-dihydro-2H-imidazo[4,5-b]pyrazine-2-thione 
• 79100-22-4 5,6-dichloro-1,3-dihydro-2H-imidazo[4,5-b]pyrazine-2-thione 
• 79100-23-5 1,2,5,6-tetrachloro-1H-imidazo[4,5-b]pyrazine 
• 79100-24-6 5,6-dichloro-2-(methylsulfanyl)-1H-imidazo[4,5-b]pyrazine