3-Boc-amino-2,6-dioxopiperidine supplier

Name
3-Boc-amino-2,6-dioxopiperidine
EINECS
CAS No. 31140-42-8
Article Data26
CAS DataBase
Density 1.2 g/cm³
Solubility
Melting Point 193.7-194.4 °C
Formula C₁₀H₁₆N₂O₄
Boiling Point 423 °C at 760 mmHg
Molecular Weight 228.248
Flash Point 209.6 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 2,6-Dioxo-3-piperidinecarbamic acid tert-butyl ester;carbamic acid, N-(2,6-dioxo-3-piperidinyl)-, 1,1-dimethylethyl ester;
PSA 84.50000
LogP 1.03600

Synthetic route

: 85535-45-1
5-amino-2-(tert-butoxycarbonylamino)-5-oxo-pentanoic acid

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With dicyclohexyl-carbodiimide In N,N-dimethyl-formamide at 80℃;	99%
With dmap; triethylamine; 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 72h;	90%
With dmap; 1,1'-carbonyldiimidazole In tetrahydrofuran for 16h; Reflux;	88%

: 120341-33-5
1-[(tert-butoxy)-carbonyl-amino]propane-1,3-dicarboxylic acid

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With 2,2,2-trifluoroacetamide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine at 20℃;	95%
With 2,2,2-trifluoroacetamide; TEA; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In dichloromethane

: 24424-99-5
di-tert-butyl dicarbonate

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

Conditions

Conditions	Yield
Stage #1: rac-α-aminoglutarimide hydrochloride With triethylamine In dichloromethane at 50℃; for 0.5h; Sealed tube; Microwave irradiation; Stage #2: di-tert-butyl dicarbonate In dichloromethane at 0℃; for 0.5h;	87%

: 13726-85-7
Boc-Gln-OH

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With dmap; 1,1'-carbonyldiimidazole In tetrahydrofuran for 17h; Heating;	76%
With dmap; 1,1'-carbonyldiimidazole In tetrahydrofuran for 24h; Heating;	76%
With dmap; 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; Inert atmosphere; Reflux;	76%

: Boc-glutamine methyl ester

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With 1-hydroxy-pyrrolidine-2,5-dione; diisopropyl-carbodiimide In tetrahydrofuran for 48h; Reflux;	66.2%

: 4976-88-9
(S)-methyl 5-amino-2-(tert-butoxycarbonylamino)-5-oxopentanoate

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With dmap; 1,1'-carbonyldiimidazole In tetrahydrofuran for 48h; Reflux;	64%

: 24424-99-5
di-tert-butyl dicarbonate

: 3-aminopiperidine-2,6-dione hydrochloric acid salt

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 8h;	58%

: 1218991-05-9
glutamine methyl ester

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium hydrogencarbonate / water; methanol / 15 h / 20 °C 2: diisopropyl-carbodiimide; 1-hydroxy-pyrrolidine-2,5-dione / tetrahydrofuran / 48 h / Reflux View Scheme

: 56-85-9, 585-21-7, 5959-95-5, 6899-04-3
GLUTAMINE

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: thionyl chloride / 8 h / 0 °C / Reflux 2: sodium hydrogencarbonate / water; methanol / 15 h / 20 °C 3: diisopropyl-carbodiimide; 1-hydroxy-pyrrolidine-2,5-dione / tetrahydrofuran / 48 h / Reflux View Scheme

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 76-05-1
trifluoroacetic acid

: (RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate

Conditions

Conditions	Yield
at 20℃; for 0.5h;	100%
In dichloromethane at 25℃;	99%
In dichloromethane at 20℃; for 4h;	98%

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: (RS)-2,6-dioxopiperidin-3-yl-ammonium trifluoroacetate

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 4h;	99%

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 24666-56-6
rac-α-aminoglutarimide hydrochloride

Conditions

Conditions	Yield
With hydrogenchloride In methanol; water for 2h;	99%

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 2353-44-8
(+/-)-α-aminoglutarimide

Conditions

Conditions	Yield
With water; sodium chloride for 4h; Time; Reflux;	98%
With trifluoroacetic acid In dichloromethane
With trifluoroacetic acid In dichloromethane at 0 - 20℃;
With trifluoroacetic acid In dichloromethane at 20℃;
With hydrogenchloride In tert-butyl methyl ether; water at 0℃; for 0.333333h;	9.5 g

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 90802-45-2
3-aminopiperidine-2,6-dione hydrobromide

Conditions

Conditions	Yield
With hydrogen bromide; acetic acid at 20℃; for 0.5h;	98%
With hydrogen bromide; acetic acid at 20℃; for 0.5h;	98%

: 641-70-3
3-nitrophthalic acid anhydride

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 19171-18-7
4-NT

Conditions

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	95%
With sodium acetate; acetic acid for 6h; Reflux;

: 826-62-0, 85081-15-8, 85081-16-9
5-norbornene-2,3-dicarboxylic anhydride

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 14166-22-4, 14166-24-6
2-(2,6-dioxopiperidin-3-yl)-3a,4,7,7a-tetrahydro-1H-4,7-methanoisoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	94%

: 27550-59-0
4-hydroxyphthalic anhydride

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 64567-60-8
5-Hydroxythalidomide

Conditions

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	91%

: 85-44-9
phthalic anhydride

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 50-35-1
thalidomide

Conditions

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Reagent/catalyst; Microwave irradiation;	91%
In 2,2,2-trifluoroethanol at 150℃; for 2h; Solvent;	91%
With sodium acetate; acetic acid for 6h; Reflux;

: 652-39-1
3-fluorophthalic anhydride

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 2‐(2,6‐dioxopiperidin‐3‐yl)‐4‐fluoroisoindoline‐1,3‐dione

Conditions

Conditions	Yield
With sodium acetate In acetic acid for 6h; Reflux;	89%
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	69%
With sodium acetate; acetic acid for 6h; Reflux;

: 37418-88-5
3-hydroxyphthalic anhydride

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 5054-59-1
4-Hydroxythalidomide

Conditions

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	86%

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 85-42-7
1,2-Cyclohexanedicarboxylic acid-anhydride

: 14166-19-9
cis-2-(2,6-dioxopiperidin-3-yl)hexahydro-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	86%

: 85-44-9
phthalic anhydride

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 2-(2,6-dioxopiperidin-3-yl)hexahydro-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
In 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation;	86%

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 74-88-4
methyl iodide

: tert-butyl N-(1-methyl-2,6-dioxopiperidin-3-yl)carbamate

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 3h;	84%
With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0 - 20℃; for 1.5h;	71%
Stage #1: (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester With sodium hydride In N,N-dimethyl-formamide at 0 - 20℃; for 0.583333h; Stage #2: methyl iodide In N,N-dimethyl-formamide at 20℃; for 2h;	66%

: 32703-79-0
4-tert-butylphthalic anhydride

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 5-(tert-butyl)-2-(2,6-dioxopiperidin-3-yl)isoindoline-1,3-dione

Conditions

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	83%

: 81-84-5
1,8-Naphthalic anhydride

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 14656-93-0
2-(2,6-dioxopiperidin-3-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione

Conditions

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 6h; Microwave irradiation; Sealed tube;	80%

: 17395-99-2
3-aminophthalic anhydride

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 19171-19-8
pomalidomide

Conditions

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	80%

: 86-90-8
4-bromophthalic anhydride

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 26166-92-7
5-bromo-2-(2,6-dioxopiperidin-3-yl)-2,3-dihydro-1H-isoindole-1,3-dione

Conditions

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	75%

: 19438-61-0
4-methylphthalic anhydride

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 40313-92-6
2-(2,6-dioxopiperidin-3-yl)-5-methylisoindoline-1,3-dione

Conditions

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	74%

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 85-43-8
1,2,3,6-Tetrahydrophthalic anhydride

: 14166-18-8
2-(2,6-dioxopiperidin-3-yl)-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione

Conditions

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	73%

: 50-00-0
formaldehyd

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 1320352-96-2
1-hydroxymethyl-3-(tert-butoxycarbonylamino)-2,6-dioxopiperidine

Conditions

Conditions	Yield
In water for 0.5h; Inert atmosphere; Reflux;	72.9%

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 552-30-7
trimellitic Anhydride

: 2-(2,6-dioxopiperidin-3-yl)-1,3-dioxoisoindoline-5-carboxylic acid

Conditions

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation; Sealed tube;	66%

: 76513-69-4
(2-trimethylethylsilylethoxy)methyl chloride

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: tert-butyl (2,6-dioxo-1-((2-(trimethylsilyl)ethoxy)methyl)piperidin-3-yl)carbamate

Conditions

Conditions	Yield
Stage #1: (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.25h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide at 20℃; for 1h;	65%
Stage #1: (RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 0.25h; Stage #2: (2-trimethylethylsilylethoxy)methyl chloride In N,N-dimethyl-formamide; mineral oil at 20℃; for 1h;	65%

: 31140-42-8
(RS)-(2,6-dioxopiperidin-3-yl)carbamic acid tert-butyl ester

: 88-99-3
benzene-1,2-dicarboxylic acid

: 50-35-1
thalidomide

Conditions

Conditions	Yield
With 2,2,2-trifluoroethanol at 150℃; for 2h; Microwave irradiation;	62%

3-Boc-amino-2,6-dioxopiperidine Specification

The CAS register number of 3-Boc-amino-2,6-dioxopiperidine is 31140-42-8. It also can be called as 2,6-Dioxo-3-piperidinecarbamic acid tert-butyl ester and the IUPAC name about this chemical is tert-butyl N-(2,6-dioxopiperidin-3-yl)carbamate. The molecular formula about this chemical is C₁₀H₁₆N₂O₄and the molecular weight is 228.25. It belongs to the Pharmacetical.

Physical properties about 3-Boc-amino-2,6-dioxopiperidine are: (1)ACD/LogP: 0.73; (2)ACD/LogD (pH 5.5): 0.73; (3)ACD/LogD (pH 7.4): 0.73; (4)ACD/BCF (pH 5.5): 2.1; (5)ACD/BCF (pH 7.4): 2.1; (6)ACD/KOC (pH 5.5): 59.16; (7)ACD/KOC (pH 7.4): 59.11; (8)#H bond acceptors: 6; (9)#H bond donors: 2; (10)#Freely Rotating Bonds: 3; (11)Polar Surface Area: 66.92Å²; (12)Index of Refraction: 1.499; (13)Molar Refractivity: 55.67 cm³; (14)Molar Volume: 189.3 cm³; (15)Polarizability: 22.07x10^-24cm³; (16)Surface Tension: 44 dyne/cm; (17)Enthalpy of Vaporization: 67.72 kJ/mol; (18)Boiling Point: 423 °C at 760 mmHg; (19)Vapour Pressure: 2.32E-07 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C1NC(=O)CCC1NC(=O)OC(C)(C)C
(2)InChI: InChI=1/C10H16N2O4/c1-10(2,3)16-9(15)11-6-4-5-7(13)12-8(6)14/h6H,4-5H2,1-3H3,(H,11,15)(H,12,13,14)
(3)InChIKey: TUGRLMXVKASPTN-UHFFFAOYAD
(4)Std. InChI: InChI=1S/C10H16N2O4/c1-10(2,3)16-9(15)11-6-4-5-7(13)12-8(6)14/h6H,4-5H2,1-3H3,(H,11,15)(H,12,13,14)
(5)Std. InChIKey: TUGRLMXVKASPTN-UHFFFAOYSA-N

Product Name

3-Boc-amino-2,6-dioxopiperidine

Synthetic route

3-Boc-amino-2,6-dioxopiperidine Specification

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