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Basic Information
CAS No.: 113451-59-5
Name: (1S,4S)-2-BOC-2,5-DIAZABICYCLO[2.2.1]HEPTANE
Molecular Structure:
Molecular Structure of 113451-59-5 ((1S,4S)-2-BOC-2,5-DIAZABICYCLO[2.2.1]HEPTANE)
Formula: C10H18N2O2
Molecular Weight: 294.372
Synonyms: 1,1-Dimethylethyl(S,S)-2,5-diazabicyclo[2.2.1]heptane-5-carboxylate;N-Boc-(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane;tert-Butyl(1S,4S)-(-)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate;tert-Butyl(1S,4S)-2,5-diazabicyclo[2.2.1]heptane-2-carboxylate;2,5-Diazabicyclo[2.2.1]heptane-2-carboxylicacid, 1,1-dimethylethyl ester, (1S)-;(1S,4S)-(-)-2-Boc-2,5-diazabicyclo[2.2.1]heptane;(1S,4S)-2,5-Diazabicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester;(1S,4S)-N-Boc-2,5-diazabicyclo[2.2.1]heptane;(1S,4S)-tert-Butyl2,5-diazabicyclo[2.2.1]heptane-2-carboxylate;
EINECS: -0
Density: 1.105 g/cm3
Melting Point: 74-76 °C(lit.)
Boiling Point: 276.372 °C at 760 mmHg
Flash Point: 120.946 °C
Solubility: Insoluble in water.
Appearance: White to slightly beige powder
Risk Codes: 34
Safety: 22-24/25
PSA: 41.57000
LogP: 1.23430
Related products
Synthetic route
113451-54-0

(2S,4R)-2-(azidomethyl)-1-(tert-butoxycarbonyl)-4-<(methylsulfonyl)oxy>pyrrolidine

113451-59-5

(1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With hydrogen; palladium on activated charcoal In methanol100%
Stage #1: (2S,4R)-2-(azidomethyl)-1-(tert-butoxycarbonyl)-4-<(methylsulfonyl)oxy>pyrrolidine With triphenylphosphine In tetrahydrofuran at 20℃; for 2h; Staudinger Azide Reduction;
Stage #2: With water In tetrahydrofuran for 18h;		71%
132666-68-3

(1S,4S)-5-Benzyl-2-tert-butoxycarbonyl-2,5-diazabicyclo<2.2.1>heptane

113451-59-5

(1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With palladium hydroxide 10 wt. % on activated carbon; hydrogen In methanol under 3102.97 Torr;90%
With palladium 10% on activated carbon; hydrogen In methanol at 50℃; under 22502.3 Torr; for 16h;85%
With 10% palladium on carbon; hydrogen76%
With palladium 10% on activated carbon; hydrogen In dichloromethane under 3102.97 Torr;10.4 g
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tert-butyl (2S,4S)-4-amino-2-(hydroxymethyl)pyrrolidin-1-carboxylate

113451-59-5

(1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 22 - 25℃; for 12h; Inert atmosphere;80.6%
40216-83-9

L-4-hydroxyproline methyl ester hydrochloride

113451-59-5

(1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: triethylamine / dichloromethane / 17 h / 0 °C
2.1: lithium borohydride / tetrahydrofuran / 26 h / 0 - 20 °C
3.1: pyridine / dichloromethane / 18 h / 40 °C
4.1: trimethylsilylazide; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 70 °C
5.1: triethylamine / dichloromethane / 0.5 h / 0 °C
6.1: triphenylphosphine / tetrahydrofuran / 2 h / 20 °C
6.2: 18 h
View Scheme
51-35-4

4R-4-hydroxyproline

113451-59-5

(1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: thionyl chloride; hydrogenchloride / water / 18 h / 20 °C / Reflux
2.1: triethylamine / dichloromethane / 17 h / 0 °C
3.1: lithium borohydride / tetrahydrofuran / 26 h / 0 - 20 °C
4.1: pyridine / dichloromethane / 18 h / 40 °C
5.1: trimethylsilylazide; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 70 °C
6.1: triethylamine / dichloromethane / 0.5 h / 0 °C
7.1: triphenylphosphine / tetrahydrofuran / 2 h / 20 °C
7.2: 18 h
View Scheme
Multi-step reaction with 6 steps
1.1: sodium carbonate / water
1.3: 20 h
2.1: toluene / Reflux
3.1: hydrogen bromide
4.1: sodium methylate / methanol / 20 °C
5.1: triethylamine / dichloromethane / 0 - 20 °C
6.1: hydrogen; palladium hydroxide 10 wt. % on activated carbon / methanol / 3102.97 Torr
View Scheme
74844-91-0

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

113451-59-5

(1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: lithium borohydride / tetrahydrofuran / 26 h / 0 - 20 °C
2.1: pyridine / dichloromethane / 18 h / 40 °C
3.1: trimethylsilylazide; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 70 °C
4.1: triethylamine / dichloromethane / 0.5 h / 0 °C
5.1: triphenylphosphine / tetrahydrofuran / 2 h / 20 °C
5.2: 18 h
View Scheme
Multi-step reaction with 4 steps
1: triethylamine / dichloromethane / 2 h / 5 - 25 °C
2: sodium azide / N,N-dimethyl-formamide / 3 h / 90 °C
3: potassium borohydride; lithium chloride / tetrahydrofuran / 12 h / 25 °C
4: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 22 - 25 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1: sodium tetrahydroborate / methanol / 18 h / 20 - 35 °C / Cooling with ice; Large scale
2: triethylamine / dichloromethane / 1 h / 20 - 35 °C / Cooling with liquid nitrogen; Large scale
3: 3 h / 80 °C / Large scale
4: palladium 10% on activated carbon; hydrogen / methanol / 16 h / 50 °C / 22502.3 Torr
View Scheme
61478-26-0

tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate

113451-59-5

(1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: pyridine / dichloromethane / 18 h / 40 °C
2.1: trimethylsilylazide; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 70 °C
3.1: triethylamine / dichloromethane / 0.5 h / 0 °C
4.1: triphenylphosphine / tetrahydrofuran / 2 h / 20 °C
4.2: 18 h
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 1 h / 20 - 35 °C / Cooling with liquid nitrogen; Large scale
2: 3 h / 80 °C / Large scale
3: palladium 10% on activated carbon; hydrogen / methanol / 16 h / 50 °C / 22502.3 Torr
View Scheme
194089-91-3

tert-butyl (2S,4R)-4-hydroxy-2-({[(4-methylphenyl)sulfonyl]oxy}methyl)-pyrrolidine-1-carboxylate

113451-59-5

(1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: trimethylsilylazide; tetrabutyl ammonium fluoride / tetrahydrofuran / 18 h / 70 °C
2.1: triethylamine / dichloromethane / 0.5 h / 0 °C
3.1: triphenylphosphine / tetrahydrofuran / 2 h / 20 °C
3.2: 18 h
View Scheme
114676-96-9

(2S,4R)-tert-butyl 2-(azidomethyl)-4-hydroxypyrrolidine-1-carboxylate

113451-59-5

(1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: triethylamine / dichloromethane / 0.5 h / 0 °C
2.1: triphenylphosphine / tetrahydrofuran / 2 h / 20 °C
2.2: 18 h
View Scheme
84520-68-3

N-tert-butoxycarbonyl-cis-4-azido-L-proline methyl ester

113451-59-5

(1S,4S)-2,5-Diaza-bicyclo[2.2.1]heptane-2-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium borohydride; lithium chloride / tetrahydrofuran / 12 h / 25 °C
2: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 22 - 25 °C / Inert atmosphere
View Scheme
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Chemistry

Systematic Name: tert-Butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
Synonyms of (1S,4S)-(-)-2-Boc-2,5-Diazabicyclo[2.2.1]heptane (CAS NO.113451-59-5): (1S,4S)-N-(tert-Butoxycarbonyl)-2,5-diazabicyclo[2.2.1]heptane ; tert-butyl 2,5-diazabicyclo[2.2.1]heptane-2-carboxylate
CAS NO: 113451-59-5
Molecular Formula: C10H18N2O2
Molecular Weight: 198.26
Molecular Structure:
H bond acceptors: 4
H bond donors: 1
Freely Rotating Bonds: 2
Polar Surface Area: 32.78 Å2
Index of Refraction: 1.5
Molar Refractivity: 52.84 cm3
Molar Volume: 179.4 cm3
Surface Tension: 37.3 dyne/cm
Density: 1.104 g/cm3
Flash Point: 120.9 °C
Enthalpy of Vaporization: 51.49 kJ/mol
Boiling Point: 276.4 °C at 760 mmHg
Vapour Pressure: 0.00482 mmHg at 25°C
Melting point: 74-76 ºC
Alpha : -44 º (c=1 in chloroform)
Appearance: (1S,4S)-(-)-2-Boc-2,5-Diazabicyclo[2.2.1]heptane (CAS NO.113451-59-5) is white to slightly beige powder .
SMILES: O=C(OC(C)(C)C)N1CC2NCC1C2
InChI: InChI=1/C10H18N2O2/c1-10(2,3)14-9(13)12-6-7-4-8(12)5-11-7/h7-8,11H,4-6H2,1-3H3
InChIKey: UXAWXZDXVOYLII-UHFFFAOYAY
Std. InChI: InChI=1S/C10H18N2O2/c1-10(2,3)14-9(13)12-6-7-4-8(12)5-11-7/h7-8,11H,4-6H2,1-3H3
Std. InChIKey: UXAWXZDXVOYLII-UHFFFAOYSA-N

Safety Profile

Safety Statements: 22-24/25 
S22: Do not breathe dust. 
S24/25: When (1S,4S)-(-)-2-Boc-2,5-Diazabicyclo[2.2.1]heptane (CAS NO.113451-59-5) is used,avoid contact with skin and eyes.
WGK Germany: 3