188111-79-7

Basic information

• Product Name: (R)-1-Boc-3-Aminopiperidine
• Synonyms: tert-Butyl (3R)-3-aminopiperidine-1-carboxylate;(R)-3-Aminopiperidine, N1-BOC protected;(R)-1-t-Butyloxycarbonyl-3-aminopiperidine hydrochloride;(R)-1-Boc-3-piperidinamine, tert-Butyl (R)-3-amino-1-piperidinecarboxylate;(3R)-3-Aminopiperidine, N1-BOC protected;(3R)-3-Amino-N1-Boc-piperidine;(R)-1-Boc-3-aMinopiperidi...;(R)-1-Boc-3-AMinopiperidin
• CAS NO: 188111-79-7
• Molecular Formula: C₁₀H₂₀N₂O₂
• Molecular Weight: 200.28
• EINECS: 1312995-182-4
• Product Categories: AMINOACID;pharmacetical;Piperidine;Piperidine Series;Piperidines;CHIRAL CHEMICALS
• Mol File: 188111-79-7.mol

Chemical Properties

• Boiling Point: 277.3 °C at 760 mmHg
• Flash Point: 121.5 °C
• Appearance: Colorless to pale yellow/Liquid
• Density: 1.041g/cm3
• Vapor Pressure: 0.00456mmHg at 25°C
• Refractive Index: 1.4730
• Storage Temp.: Store under inert gas
• Solubility: Chloroform (Slightly), DMF (Slightly), DMSO (Slightly)
• PKA: 10.35±0.20(Predicted)
• Water Solubility: Immiscible with water.
• Sensitive: Moisture Sensitive
• CAS DataBase Reference: (R)-1-Boc-3-Aminopiperidine(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-1-Boc-3-Aminopiperidine(188111-79-7)
• EPA Substance Registry System: (R)-1-Boc-3-Aminopiperidine(188111-79-7)

Safety Data

• Hazard Codes: Xn
• Statements: 22-36/37/38
• Safety Statements: 26
• RIDADR: UN2735
• WGK Germany: 3
• F: 10-34
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 188111-79-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-1-Boc-3-Aminopiperidine is used as an intermediate for the synthesis of various pharmaceuticals. Its unique structure allows it to be a key component in the development of new drugs with potential therapeutic applications.
Used in CBP/P300 Bromodomain Inhibition:
(R)-1-Boc-3-Aminopiperidine is used as a precursor to prepare a benzoxazepine derivative named (R)-7-(3,5-dimethoxyphenyl)-N-(piperidin-3-yl)-4-propionyl-2,3,4,5-tetrahydro-1,4-benzoxazepine-9-carboxamide. This derivative acts as a potent CBP/P300 bromodomain inhibitor, which can have significant implications in the treatment of various diseases by modulating gene expression and cellular processes.
Used in Antidiabetic Agent Synthesis:
(R)-1-Boc-3-Aminopiperidine can be used as a precursor for the preparation of dipeptidyl peptidase IV (DPP-IV) inhibitors like linagliptin and alogliptin. These inhibitors play a crucial role in the management of type 2 diabetes by reducing the rate at which glucose is released into the bloodstream, thus helping to maintain healthy blood sugar levels.

InChI:InChI=1/C10H20N2O2/c1-10(2,3)14-9(13)12-6-4-5-8(11)7-12/h8H,4-7,11H2,1-3H3/t8-/m0/s1

Synthetic route

tert-butyl (3R)-3-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate (320580-76-5) → tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7)

Conditions	Yield
Pd-C In methanol	99%

C10H18N2O2 → tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7)

Conditions	Yield
With bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; C13H18FeP2; hydrogen; sodium hydride In dichloromethane Large scale;	95.2%

(R)-tert-butyl 3-carbamoylpiperidine-1-carboxylate (915226-43-6) → tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7)

Conditions	Yield
With sodium hypochlorite; sodium hydroxide In water at 15 - 25℃; for 16h;	80%

3-oxo-piperidine-1-carboxylic acid tert-butyl ester (98977-36-7) → tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7)

Conditions	Yield
With pyridoxal 5'-phosphate; immobilized Codex® amine ω-transaminase; isopropylamine In dimethyl sulfoxide at 50℃; pH=7.5; Temperature; Enzymatic reaction; enantioselective reaction;	70%
Multi-step reaction with 2 steps 1: ammonium acetate / ethanol / 7 h / Reflux; Large scale 2: bis(1,5-cyclooctadiene)rhodium(I) tetrafluoroborate; sodium hydride; C13H18FeP2; hydrogen / dichloromethane / Large scale View Scheme

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 6-methylimidazo<2,1-b>thiazole-5-carboxylic acid (77628-51-4) → (R)-3-[(6-methyl-imidazo[2,1-b]thiazole-5-carbonyl)-amino]-piperidine-1-carboxylic acid tert-butyl ester (1030389-10-6)

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 20h;	100%
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 20h;	100%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 3,5-dichloro-pyrazine-2-carbonitrile (313339-92-3) → tert-butyl (3R)-3-[(6-chloro-5-cyanopyrazin-2-yl)amino]piperidine-1-carboxylate (1207852-79-6)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 1h;	100%
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 20 - 50℃;	60%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 3-(4-chloro-5-nitropyrimidin-2-yl)-6-fluoroimidazo[1,2-a]pyridine (1313279-53-6) → (R)-tert-butyl 3-(2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)-5-nitropyrimidin-4-ylamino)piperidine-1-carboxylate (1313279-69-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 20℃;	100%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 2-chloroethyl isothiocyanate (1943-83-5) → tert-butyl (3R)-3-{[(2-chloroethyl)carbamoyl]amino}piperidine-1-carboxylate

Conditions	Yield
With triethylamine In dichloromethane for 4.41667h;	100%
With triethylamine In 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran at 20℃; for 4h;	81.5%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 4-methoxybenzoic acid (100-09-4) → (R)-tert-butyl 3-(4-methoxybenzamido)piperidine-1-carboxylate

Conditions	Yield
With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In 1,4-dioxane; N,N-dimethyl-formamide at 20℃; for 3h;	100%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 3-(4,6-dichloro-5-fluoropyrimidin-2-yl)pyrazolo[1,5-a]pyridine → tert-butyl (3R)-3-[(6-chloro-5-fluoro-2-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-4-yl)amino]piperidine-1-carboxylate

Conditions	Yield
With triethylamine In ethanol at 80℃; for 48h;	100%
With triethylamine In ethanol at 80℃; for 48h;	100%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 2-bromothiazole-5-carbonitrile (440100-94-7) → C14H20N4O2S

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 80℃; for 6h;	100%
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 80℃; for 6h;

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + N-(2-methoxypyridin-3-yl)-5-nitro-4-thiocyanatopyrimidin-2-amine (1414805-24-5) → (R)-tert-butyl 3-(2-(2-methoxypyridin-3-ylamino)-5-nitropyrimidin-4-ylamino)piperidine-1-carboxylate (1415151-88-0)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In tetrahydrofuran at 50℃;	100%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 2-[(6-chloro-3-methyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-1-yl)methyl]-4-fluorobenzonitrile (865759-24-6) → C23H28FN5O4

Conditions	Yield
With sodium hydrogencarbonate In acetonitrile for 20h; Reflux;	99.2%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 3-(4,5-dichloropyrimidin-2-yl)-6-fluoroimidazo[1,2-a]pyridine (1313006-75-5) → tert-butyl (3R)-3-{[5-chloro-2-(6-fluoroimidazo[1,2-a]pyridin-3-yl)pyrimidin-4-yl]amino}piperidine-1-carboxylate (1313006-78-8)

Conditions	Yield
In ethanol for 18h; Reflux;	99%
In ethanol for 18h; Reflux;	99%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) → 3-(R)-aminopiperidine dihydrochloride (943528-10-7)

Conditions	Yield
With hydrogenchloride In ethanol for 2h; Large scale;	99%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 9-chloro-6-ethoxy-7-methoxy-1H,2H,3H-cyclopenta[b]quinoline → tert-butyl (3R)-3-({6-ethoxy-7-methoxy-1H,2H,3H-cyclopenta[b]quinolin-9-yl}amino)piperidine-1-carboxylate

Conditions	Yield
With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate In 1,4-dioxane at 110℃; for 2h; Buchwald-Hartwig Coupling;	99%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + ethyl 2-methyl-5-chloropyrazolo[1,5-a]pyrimidine-3-carboxylate (1431654-56-6) → ethyl (R)-5-((1-(tert-butoxycarbonyl)piperidin-3-yl)amino)-2-methylpyrazolo[1,5-a]pyrimidine-3-carboxylate

Conditions	Yield
With potassium fluoride at 100℃; for 2h;	99%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + ethyl 4-chloro-7H-pyrrolo[2,3-d]pyrimidine-5-carboxylate (144927-57-1) → C19H27N5O4

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In butan-1-ol at 135℃; for 1h; Sealed tube;	99%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + (4,6-dichloropyrimidin-5-yl)(4-phenoxyphenyl)methanone → (R)-tert-butyl 3-((6-chloro-5-(4-phenoxybenzoyl)pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 24h;	98.1%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) → 3-(R)-aminopiperidine dihydrochloride

Conditions	Yield
With hydrogenchloride In isopropyl alcohol	98%
With acetyl chloride In ethanol at 0 - 20℃;

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (90213-66-4) → tert-butyl (R)-3-((2-chloro-7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 110℃; for 12h;	98%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + acryloyl chloride (814-68-6) → tert-butyl (3R)-3-(prop-2-Enoylamino)piperidine-1-carboxylate

Conditions	Yield
With triethylamine at 25℃; for 2h;	97.3%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + methanol (67-56-1) + 1,1'-carbonyldiimidazole (530-62-1) → (R)-tert-butyl 3-((methoxycarbonyl)amino)piperidine-1-carboxylate

Conditions	Yield
Stage #1: methanol; 1,1'-carbonyldiimidazole With triethylamine In tetrahydrofuran at 20℃; for 0.166667h; Inert atmosphere; Stage #2: tert-butyl (3R)3-aminopiperidine-1-carboxylate In tetrahydrofuran at 75℃; for 12h;	97%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 9-chloro-6,7-bis(2H3)methoxy-1H,2H,3H-cyclopenta[b]quinoline → tert-butyl (3R)-3-{[6,7-bis(2H3)methoxy-1H,2H,3H-cyclopenta[b]quinolin-9-yl]amino}piperidine-1-carboxylate

Conditions	Yield
With chloro[2-(dicyclohexylphosphino)-3,6-dimethoxy-2′,4′,6′-tri-1-propyl-1,1′-biphenyl][2-(2-aminoethyl)phenyl]palladium(II); sodium t-butanolate In 1,4-dioxane at 100℃; for 1h; Buchwald-Hartwig Coupling; Sealed tube;	97%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + (4,6-dichloropyrimidin-5-yl)(4-ethoxyphenyl)methanone → (R)-tert-butyl 3-((6-chloro-5-(4-ethoxybenzoyl)pyrimidin-4-yl)amino)piperidine-1-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 20℃; for 24h;	96%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 5,7-dichloro-3-iso-propyl-pyrazolo[1,5-a]pyrimidine (771510-32-8) → (R)-3-((5-chloro-3-isopropylpyrazolo[1,5-a]pyrimidin-7-yl)amino)piperidine-1-carboxylic acid tert-butyl ester

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In ethanol at 85℃;	96%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 3-(4,6-dichloropyrimidin-2-yl)pyrazolo[1,5-a]pyridine → tert-butyl (3R)-3-[(6-chloro-2-pyrazolo[1,5-a]pyridin-3-ylpyrimidin-4-yl)amino]piperidine-1-carboxylate

Conditions	Yield
With triethylamine In ethanol for 64h; Reflux;	95%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → tert-butyl (3R)-3-{[(Z)-amino(imino)methyl]amino}piperidine-1-carboxylate hydrochloride (885049-13-8)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 60℃; for 6h;	94%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 1H-pyrazole-1-carboximidamide hydrochloride (4023-02-3) → tert-butyl (3R)-3-{[amino(imino)methyl]amino}piperidine-1-carboxylate hydrochloride

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 70℃; for 18h;	94%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 5-bromo-2-(tetrahydro-2H-pyran-2-yl)-2H-indazole (1178903-21-3) + 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl (76144-87-1, 76189-55-4, 76189-56-5, 136655-44-2, 98327-87-8) → (R)-tert-butyl 3-(phenylamino)piperidine-1-carboxylate (1178903-50-8) + (3R)-tert-butyl 3-(2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-5-ylamino)piperidine-1-carboxylate (1178903-52-0)

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); sodium t-butanolate In tetrahydrofuran at 55℃; for 18h; Buchwald coupling; Inert atmosphere;	A n/a B 94%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 7-chloro-1-methyl-1H-pyrrolo[2,3-c]pyridine (875340-57-1) → (R)-tert-butyl 3-((1-methyl-1H-pyrrolo[2,3-c]pyridin-7-yl)amino)piperidine-1-carboxylate

Conditions	Yield
With tris-(dibenzylideneacetone)dipalladium(0); dicyclohexyl-(2′,4′,6′-triisopropyl-3,6-dimethoxy-[1,1′-biphenyl]-2-yl)phosphine; sodium t-butanolate In toluene at 105℃; for 3h; Inert atmosphere;	94%

tert-butyl (3R)3-aminopiperidine-1-carboxylate (188111-79-7) + 4-bromo-2-nitrobenzoic acid (99277-71-1) → (R)-tert-butyl 3-(4-bromo-2-nitrobenzamido)piperidine-1-carboxylate

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 10 - 35℃; for 4h;	94%

Upstream product

• 320580-76-5 tert-butyl (3R)-3-{[(benzyloxy)carbonyl]amino}piperidine-1-carboxylate 
• 915226-43-6 (R)-tert-butyl 3-carbamoylpiperidine-1-carboxylate 
• 98977-36-7 3-oxo-piperidine-1-carboxylic acid tert-butyl ester 

Downstream Products

• 1009633-72-0 C₁₆H₂₂N₄O₈S 
• 1062132-47-1 (R)-tert-butyl 3-(4-tert-butylbenzamido)piperidine-1-carboxylate 
• 1159996-27-6 (3R)-tert-butyl 3-(1-(4-(trifluoromethyl)phenyl)-1,2,3,4-tetrahydroisoquinoline-2-carboxamido)piperidine-1-carboxylate 
• 1044561-53-6 tert-Butyl (3R)-3-[(4-chlorophenyl)amino]piperidine-1-carboxylate 
• 1178903-51-9 (R)-tert-butyl 3-(p-tolylamino)piperidine-1-carboxylate 
• 1178903-19-9 (R)-tert-butyl 3-(1-(4-methoxybenzyl)-1H-indazol-5-ylamino)piperidine-1-carboxylate 
• 1178903-50-8 (R)-tert-butyl 3-(phenylamino)piperidine-1-carboxylate 
• 1035097-02-9 (3R)-tert-butyl 3-(1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-ylamino)piperidine-1-carboxylate 
• 1178903-20-2 (R)-tert-butyl 3-(2-(4-methoxybenzyl)-2H-indazol-5-ylamino)piperidine-1-carboxylate 
• 1178903-52-0 (3R)-tert-butyl 3-(2-(tetrahydro-2H-pyran-2-yl)-2H-indazol-5-ylamino)piperidine-1-carboxylate 
• 334618-23-4 3-(R)-aminopiperidine dihydrochloride 
• 1240515-15-4 C₁₈H₂₆N₂O₃ 
• 1276045-20-5 (R)-N-(1-(3-methoxyphenyl)piperidin-3-yl)cyclopropanecarboxamide 
• 1276045-22-7 C₁₆H₂₁ClN₂O₂ 

Relevant articles and documents

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